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

HRID 399161ノート

反応式

HRID 399161 の反応式
[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]

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 94078tert-ButyldiphenylchlorosilaneHCID 18970139rac-3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanol

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8fc73e34e5e6425d9c5a209bee189c21
出典データセット
uspto-grants-1998_10
特許番号
US05817766

反応ノート

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