Dimethylformamide → 5-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol

HRID 399161노트

반응식

HRID 399161 반응식
[OH:1][C:2]1[C:7]2[CH:8]([CH3:18])[CH:9]([CH2:14][CH2:15][CH2:16][OH:17])[C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:3]=1.CN(C=O)C.[H-].[Na+].[C:31]([Si:35](Cl)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([CH3:34])([CH3:33])[CH3:32]>CCOC(C)=O>[CH3:34][C:31]([Si:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[O:1][C:2]1[C:7]2[CH:8]([CH3:18])[CH:9]([CH2:14][CH2:15][CH2:16][OH:17])[C:10]([CH3:12])([CH3:13])[O:11][C:6]=2[CH:5]=[C:4]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:3]=1)([CH3:32])[CH3:33]

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 24758Sodium hydrideHCID 94078tert-ButyldiphenylchlorosilaneHCID 18970139rac-3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol

생성물 1

HCID 189701315-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol수율 45%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3.17 g (8.78 mmol) of rac-3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol in 60 mL of anhy. DMF (Aldrich) was added to a suspension of 383 mg (1 eq) of sodium hydride (Aldrich) in 20 mL of anhy. DMF (Aldrich) and the mixture stirred at RT under argon for 0.5 hr. 2.28 mL (1 eq.) of tert-butylchlorodiphenylsilane (Aldrich) was then added by syringe. After stirring for 2 hr at RT the reaction was diluted with EtOAc, washed with 0.1N aq. HCl, water, sat. aq. NaCl, dried and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with 30% EtOAc-hexane. The fractions containing the product were combined and evaporated under reduced pressure to give 2.23 g (45%) of 5-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-3,4-dihydro-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol as a pale yellow oil. HR EI MS: Calc M+, 558.3530; Observed, 558.3516.

후처리

  1. washwashed with 0.1N aq. HCl, water, sat. aq. NaCl
  2. customdried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel
  5. washeluting with 30% EtOAc-hexane
  6. additionThe fractions containing the product
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-8fc73e34e5e6425d9c5a209bee189c21
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05817766

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