반응식
[CH2:1]([Li])CCC.[CH3:6][Si:7]([CH3:21])([CH3:20])[CH2:8][CH2:9][O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1)=[O:12]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:11]([O-:12])(=[O:10])[CH3:13].[CH3:6][Si:7]([CH3:21])([CH3:20])[CH2:8][CH2:9][O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH2:16][C:15](=[CH2:1])[CH2:14]1)=[O:12]참가 물질
반응물 2
생성물 2
시약·촉매·용매 2
반응 조건
- 온도
- -10 °C
실험 절차
A solution of 1.6 M n-butyllithium in hexanes (14.0 mL, 22.4 mmol) was added to a heterogeneous mixture of methyltriphenylphosphonium bromide (8.02 g, 22.4 mmol) in tetrahydrofuran (50 mL) at −10° C. After stirring for 30 min at −10° C., the yellow slurry was cooled to −78° C. and 3-oxo-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester (3.41 mg, 14.1 mmol) in tetrahydrofuran (20 mL) was added. After stirring for 10 min at −78° C., the dry ice/acetone bath was removed and the heterogeneous mixture was stirred for 3 h, during which time the solution warmed to ambient temperature. The heterogeneous mixture was concentrated and the residue was flash chromatographed with 99:1, 49:1, 24:1, and 23:2 hexanes:etheyl acetate as the eluant to yield 3.38 g (100% yield) of 3-methylene-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester as a clear oil.
후처리
- temperaturethe yellow slurry was cooled to −78° C.
- stirringAfter stirring for 10 min at −78° C.
- customthe dry ice/acetone bath was removed
- stirringthe heterogeneous mixture was stirred for 3 h, during which time the solution
- temperaturewarmed to ambient temperature
- concentrationThe heterogeneous mixture was concentrated
- customchromatographed with 99:1, 49:1, 24:1, and 23:2 hexanes
출처 및 근거
- ORD 기록
- ord-2574301570b546bbbd04d4f66b8d5256
- 출처 데이터셋
- uspto-grants-2008_06
- 특허 번호
- US07385085B2
연결된 노트
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