Reaction #3106

Reaction equation

racemic inden-1-ol

vinyl acetate

→

(R)-1-acetoxyindene

Yield 38.0%

(S)-inden-1-ol

Yield 10.0%

Solvents

t-butylmethyl ether

Conditions

Workup

1. 1
   OtherAfter the end of the reaction
2. 2
   Filtrationthe suspension was filtered off
3. 3
   Otherto remove lipase
4. 4
   ConcentrationThe filtrate was concentrated

Procedure

100 mg (0.76 mmol) of racemic inden-1-ol, 0.13 mg (1.15 mmol) of vinyl acetate and 75.6 mg (100 mg of racemate/mmol) of lipase PS were suspended in 10 ml of t-butylmethyl ether and stirred at 37° C. for 7 days. After the end of the reaction, the suspension was filtered off to remove lipase. The filtrate was concentrated and the residue was subjected to silica gel column chromatography (eluate: ethyl acetate-hexane, 1:10 V/V), to separate into 50 mg (yield 38.0%, optical purity 22% ee) of (R)-1-acetoxyindene and 10 mg (yield 10.0%, optical yield 22% ee) of (S)-inden-1-ol respectively. The optical purities were determined by an analysis according to high speed liquid chromatography (column: chiral cell OD, eluate: isopropanol-hexane, 1% V/V).

Source