Pentylmagnesium chloride

In a similar way, methylene moieties can be achieved by employing siliconeo-pentylmagnesium chloride (287) to carry out a methylenation 190. If 3-pentanone (257) is treated with 287,2-ethyl-1-butene (288) is formed (Scheme 39). For further applications of the Peterson reaction and its modification, see also64,191,192. ... 

The well-known Robinson-Schbpf reaction has been applied to the synthesis of JZ-adaline (107) from ketoglutaric acid (457), ammonium chloride, and keto-aldehyde (458) (Scheme 58) 338). The second synthesis of starts with nitrone 459 462). Reaction of 459 with pentylmagnesium bromide gave a hydroxylamine (460) which was oxidized to yield a mixture of nitrones 461 and 462. Without separation of the nitrones (461 and 462), successive treatments with allylmagnesium bromide and then mercuric oxide gave a mixture of desired nitrones 466 and 467 and by-product 468. Nitrones 466 and 467 are capable of 1,3-dipolar cycloaddition and, on heating in chloroform, 466 and 467... 

CO2 + 5% MeOH, 0.92 g/ml, 365 atm, 45°C, 20 min static, 30 min dynamic, 2 ml/min Direction of fluid flow up extraction vessel orientation vertical SFE extracts collected in (i) Isco 15 ml methylene chloride, (ii) HP octadecyl-bonded silica trap and rinsed off the trap with 3 X 1.8 ml portions of methylene chloride extracts transferred to a 60 ml reparatory funnel and concentrated by nitrogen to a final volume of approximately 0.5 ml derivatization step extract treated with pentylmagnesium bromide (PMB) to convert the ionic organotin compounds into their neutral derivatives Extraction parameters studied... 

Second method ca. 0.5 g sediment was extracted with methanol/tropolone after addition of HCI. Tripropyltin was added as internal standard. Derivatiza-tion was performed by addition of pentylmagnesium bromide (2 mol L ) followed by clean-up with silica gel. Separation was by CGC (column of 25 m length, 0.2 mm internal diameter, methylphenyl silicon as stationary phase, 0.11 pm film thickness He as carrier gas at 130 mL min injector temperature at 260 °C column temperature ranging from 80 to 280 °C detector (transfer line) temperature at 280 °C). Detection was by mass spectrometry. Calibration was by calibration graph, using butyltin chloride compounds as calibrants. 

In an earlier, longer, route [115, 149], the acid chloride of (LXXIII) with acetylene and aluminium chloride followed by the action of methanolic sodium hydroxide gave the acetal (LXXVI) which on borohydride reduction and treatment with 2iV-sulphuric acid gave a mixture of two epimeric un-saturatai aldehydes. The predominant isomer of these then led to (LXXI) on reaction with pentylmagnesium bromide followed by ester hydrolysis. 

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