تفاعل #3105

معادلة التفاعل

racemic 1-acetoxyindene

acetone

→

(S)-1-acetoxyindene

المردود 44.6%

(R)-inden-1-ol

المردود 46.1%

المذيبات

phosphate

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe reaction solution was filtered on Celite
2. 2
   أخرىto remove lipase
3. 3
   استخلاصThe liltrate was extracted with diethyl ether
4. 4
   أخرىthe extracted solution was dried on magnesium sulfate
5. 5
   أخرىThe solvent was removed under a reduced pressure

الإجراء التجريبي

1.0 g (5.75 mmol) of racemic 1-acetoxyindene and 57.5 mg of lipase PS (made by Amano Seiyaku Sha, derived from Pseudomonas bacterium) were suspended in 58 ml of phosphate buffer (0.1M)-acetone mixed solution (9:1 V/V) and stirred at 37° C. for 48 hours. The reaction solution was filtered on Celite to remove lipase. The liltrate was extracted with diethyl ether and the extracted solution was dried on magnesium sulfate. The solvent was removed under a reduced pressure and the residue was subjected to silica gel column chromatography (eluate:ethyl acetate-hexane, 1:10 V/V) to separate into 446 mg (yield 44.6%) of (S)-1-acetoxyindene and 350 mg (yield 46.1%) of (R)-inden-1-ol respectively. The specific rotations and optical purities thereof were as shown below. The optical purities were determined by high speed liquid chromatography (column: chiral cell OD, eluate: isopropanol-hexane, 1% V/V).

المصدر