Triphenylmethyl ethyl ether

S-1. Preparation of Triphenylmethyl Ethyl Ether 5-2. Preparation of Allyl Phenyl Ether... 

To an Erlenmeyer flask containing 100 ml of absolute ethanol is added 27.9 gm (0.10 mole) of triphenylmethyl chloride. The flask is heated to get rid of hydrogen chloride. Upon cooling, 28.0 gm (97%) of the trityl ethyl ether separates, m.p. 83°C. 

As previously discussed, ethyl chlorocarbonate reacts rapidly and selectively with an equatorial 3-hydroxyl group to give the corresponding cathylate. Trityl ethers, usually employed as a selective protecting group for primary hydroxyls, can be prepared from A -3j3-ols by heating with triphenylmethyl chloride in pyridine, and from 5a-3 -alcohols by more prolonged heat-... 

Boron trifluoride etherate, is also a good catalyst for this hydride transfer to chalcone. Unlike triphenylmethyl perchlorate, however, chalcone is able to enter Michael additions with the 1,5-diketone followed by eliminations leading to unexpected products, e.g., 3-benzyl-2,4,6-triphenylpyrylium from 2-carbethoxy-l,3,5-tri-phenylpentane-l,5-dione and chalcone the benzyl group originates from chalcone, the elimination product being ethyl benzoylacetate. ... 

Ethyl 2,2,4-trimethyl-3-oxopentanoate. Add 24 g (28 ml, 0.21 mol) of ethyl 2-methylpropanoate b.p. 110-111 °C, to the solution of c. 0.21 mol of triphenylmethyl sodium in approximately 1400 ml of ether contained in the 2-litre twonecked flask. Stopper the flask, shake well to effect complete mixing and keep at room temperature for 60 hours. Acidify the reaction mixture by adding, with shaking, 15 ml of glacial acetic acid, and then extract with 100 ml of water. Wash the ethereal solution with 50 ml portions of 10 per cent sodium carbonate solution until free from excess acid, dry over anhydrous sodium sulphate remove the ether under reduced pressure with a rotary evaporator. Distil the residue under reduced pressure through a short fractionating column. Collect the ethyl 2,2,4-trimethyl-3-oxopentanoate at 95-96 °C/ 18mmHg the yield is 14.5 g (74%). The b.p. at atmospheric pressure is 201-202 °C. 

Triphenylmethyl ethers of sugars are important, as well as the methyl,782 ethyl, and benzyl ethers.783 For a comprehensive collection of references see Stanek et aJ.1SAr... 

Alcohols, Phenols, and Ethers. — Attempts to obtain evidence that l-(pentafluoro-phenyl)ethanoI or pentafluorobenzaldehyde ethyl acetal can act as a hydride ion donor towards triphenylmethyl fluoroborate have met with very limited success. The main products (82) and (83) of these reactions and the most likely routes to them are illustrated in Schemes 21 and 22, and although the traces of pentafluoro-... 

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