Phosphate → HCID 20073356, compound

Participants

Reaction Steps

The product from step (c) (9.5 g) was taken up in 0.1 M aqu. phosphate buffer (250 ml, pH 7) under N2 and lipase (150 mg, Fluka Cat. No. 62312) was added. As the reaction proceeded, 1 M aqu. NaOH was added from an autoburette to maintain the pH at 7 (14.5 ml added over 27 hours). After 27 hours, methylene chloride (250 ml) was added, the mixture dried over MgSO4 and stripped, and the residue eluted through a silica gel column using ether. The eluate was monitored by TLC and similar fractions combined and stripped to give (+)-(E)-1-(3-phenoxyphenyl) but-1-en-3-ol (3.7 g, [α]D20 +8.47° (c.2.72, EtOH)) and chiral (E)-1-(3-phenoxyphenyl)but-1-en-3-yl chloroacetate (3.7 g). The latter compound was taken up in methanol (50 ml), anhy. potassium carbonate (1 g) was added, and the mixture stirred for 1/2 hour. The mixture was then stripped, the residue partitioned between ether and water, and the organic phase separated, washed with satd. aqu. NaCl, and stripped to give (-)-(E)-1-(3-phenoxyphenyl)but-1-en-3-ol (2.7 g. [α]D20 -11.0° (c.2.92, EtOH)).

Provenance & Evidence