Synthesis
General procedure for the synthesis of 1-(2-chlorophenyl)ethanol from 1-(2-chlorophenyl)ethanol: 1.0 mmol of racemic alcohol (1o) was dissolved in 5 mL of dichloromethane at -30 °C and 0.01 mol/mol of a compound of formula 2 (where R is I and n is 2) was added as a catalyst. Subsequently, 0.7 equivalents of the methylsilylating agent Formula 5 (where R4 is methyl), 1 equivalent of potassium fluoride, and 80 mg of carboxylic acid-based ion exchange resin were added and the reaction mixture was stirred for 1 hour. Upon completion of the reaction, the mixture was filtered to recover the potassium fluoride and ion exchange resin, and then the filtrate was concentrated. The residue was purified by fast chromatography (eluent ratio acetone/hexane/triethylamine = 1:5:0.025) to afford the target chiral alcohol (49% yield, 98% enantiomeric excess value, (S)-configuration).
References
[1] Patent: KR2015/114167, 2015, A. Location in patent: Paragraph 0359-0360
[2] Patent: KR2015/114445, 2015, A. Location in patent: Paragraph 0354; 0355; 0356; 0442
[3] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 4, p. 1079 - 1085
[4] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 16, p. 2397 - 2402
[5] ChemCatChem, 2015, vol. 7, # 24, p. 4016 - 4020
