Tetrahydrofuran → tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-formylvalerate
반응식
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30](=[O:35])NCOC)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(O)(=O)C>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([CH:30]=[O:35])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1참가 물질
6
반응물 4
생성물 1
시약·촉매·용매 1
반응 조건
- 온도
- -78 °C
실험 절차
tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate (4.61 g) and tetrahydrofuran (60 mL) were mixed. To the mixture was added dropwise diisobutylaluminum hydride (1.0 M in toluene) (13.1 mL) at −78° C. The mixture was stirred at −78° C. for 1.5 hr. To the mixture was added dropwise acetic acid (0.515 mL). After an addition of aqueous Rochelle salt at −20° C., the mixture was extracted with ethyl acetate. The organic layer washed with water, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/25) to give the title compound (2.60 g).
후처리
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer washed with water
- dry with materialdried over magnesium sulfate
- filtrationThe magnesium sulfate was filtered off
- concentrationthe filtrate was concentrated in vacuo
- customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/25)
출처 및 근거
- ORD 기록
- ord-d4fcddd7217f4f609f18389659ed9d23
- 출처 데이터셋
- uspto-grants-2013_12
- 특허 번호
- US08604069B2
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