反应详情

50 mL of a 2M lithium isopropoxide solution in THF was placed under an argon atmosphere and 13.4 g of anhydrous lithium iodide was added thereto. After 15 minutes, 45 mL of a 1M methyltitanium isopropoxide solution in THF was added. Then the mixture was combined with 8.1 g of tert-butyl 4-cyanobenzoate and stirred for 10 minutes. Then within 60 minutes, 47.3 mL of a 15% diethylzinc solution in hexane was added thereto and the mixture was stirred for 12 hours at RT. After hydrolysis with 20 mL of water, it was stirred for a further 30 minutes, filtered off, and washed 3× with 100 mL of ether. After extraction of the organic phase with water, the mixture was evaporated down with silica gel and the substance was chromatographed with dichloromethane/methanol (98:2) at 20 mL/min on silica gel 70. Residue: 3 g oil.

1. waitThen within 60 minutes
2. stirringthe mixture was stirred for 12 hours at RT
3. stirringwas stirred for a further 30 minutes
4. filtrationfiltered off
5. washwashed 3× with 100 mL of ether
6. extractionAfter extraction of the organic phase with water
7. customthe mixture was evaporated down with silica gel
8. customthe substance was chromatographed with dichloromethane/methanol (98:2) at 20 mL/min on silica gel 70