Reaction #1458434

Reaction equation

(3R,5S) t-butyl 3,5,6-trihydroxyhexanoate

vinylacetate

→

(3R,5S) t-butyl 6-acetoxy-3,5-dihydroxyhexanoate

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherwas removed by screening
2. 2
   Otherthe volatiles removed by distillation under vacuum

Procedure

To a stirred 1 l round bottom flask 700 ml tetrahydrofuran and 70.7 g (0.32 mol) of (3R,5S) t-butyl 3,5,6-trihydroxyhexanoate, 41 ml (0.46 mol) vinylacetate and 6.3 g of the supported lipase Chirazyme L2™ were charged. After 3 hours stirring at ambient temperature the lipase was removed by screening and the volatiles removed by distillation under vacuum. The mass of crude oil was 78.7 g and the major component was determined to be (3R,5S) t-butyl 6-acetoxy-3,5-dihydroxyhexanoate. This material was used directly in the next stage.

Source