Triethylamine → 3-{[tert-Butyl(dimethyl)silyl]oxy}-4-chlorobenzaldehyde

HRID 33431ノート

反応式

HRID 33431 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[OH:10].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[Si:11]([O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[Cl:1])[CH:6]=[O:7])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 138651144-Chloro-3-hydroxybenzaldehyde

生成物 1

HCID 865980253-{[tert-Butyl(dimethyl)silyl]oxy}-4-chlorobenzaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-chloro-3-hydroxy-benzaldehyde* (0.354 g), 4-N,N-dimethylaminopyridine (0.028 g), tert-butyldimethylsilyl chloride (0.409 g) and triethylamine (0.473ml) in DCM (15 ml) was stirred at room temperature under nitrogen for 19 h. The mixture was quenched with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The combined organic extracts were concentrated under reduced pressure to give an oil which was purified using SPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate:cyclohexane) to give the title compound (0.42 g) as an oil. *Kelley, J; Linn, J; Selway, J. W. T., J. Med. Chem. (1989), 32(8), 1757-63.

後処理

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with diethyl ether
  3. concentrationThe combined organic extracts were concentrated under reduced pressure
  4. customto give an oil which
  5. customwas purified
  6. washSPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate:cyclohexane)

出典と根拠

ORDレコード
ord-e28982d99bf94fdc93b01fcf36950fb2
出典データセット
uspto-grants-2008_09
特許番号
US07429587B2

反応ノート

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