Dichloromethane → (1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl-ethyl tert-butyl(dimethyl)silyl ether

HRID 2056724ノート

反応式

HRID 2056724 の反応式
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClCCl.[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[C@H:21]([CH2:22][CH2:23][OH:24])[O:20][CH2:19][CH2:18][C:17]=2[CH:25]=1.C(N(C(C)C)CC)(C)C.CN(C1C=CC=CN=1)C>CN(C)C=O>[Si:1]([O:24][CH2:23][CH2:22][C@H:21]1[C:16]2[CH:15]=[CH:14][C:13]([Br:12])=[CH:25][C:17]=2[CH2:18][CH2:19][O:20]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

7

反応物 5

HCID 6344DichloromethaneHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 536878432-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol

生成物 1

HCID 69307753(1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl-ethyl tert-butyl(dimethyl)silyl ether

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A 1M solution of tert-butyldimethylsilyl chloride in dichloromethane (30 mL, 30 mmol) was added dropwise under nitrogen to an ice/water-cooled solution of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (6.7 g, 24.4 mmol), diisopropylethylamine (6.7 g. 51.8 mmol) and dimethylaminopyridine (0.32 g, 2.5 mmol) in dry dimethylformamide (70 mL). After stirring overnight at room temperature, the mixture was quenched with ice/water and extracted with ether (2×). The combined organic extracts were washed with water (5×), dried (MgSO4) and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/hexane (0:100 to 10:90), to give the title compound as oil.

後処理

  1. customthe mixture was quenched with ice/water
  2. extractionextracted with ether (2×)
  3. washThe combined organic extracts were washed with water (5×)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto give an oil
  7. customThis was purified by flash chromatography on silica
  8. washeluting with ethyl acetate/hexane (0:100 to 10:90)

出典と根拠

ORDレコード
ord-8bacdb707b1c4851a6b7b23db5318d1f
出典データセット
uspto-grants-2008_02
特許番号
US07335660B2

反応ノート

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