Imidazole → 5-(Tert-butyldimethylsilyloxy)-2-fluorobenzaldehyde

HRID 1012653

反応式

HRID 1012653 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.CCOC(C)=O>CN(C=O)C>[C:11]([Si:15]([CH3:17])([CH3:16])[O:10][C:7]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([CH:6]=1)[CH:4]=[O:5])([CH3:14])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 5872472-Fluoro-5-hydroxybenzaldehyde

生成物 1

HCID 138616955-(Tert-butyldimethylsilyloxy)-2-fluorobenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Compound 508 (1.5 g, 10.7 mmol) was dissolved in dry DMF (40 mL) under an argon atmosphere. tert-Butyl-chloro-dimethyl-silane (2.43 g, 16.1 mmol) and imidazole (1.1 g, 16.1 mmol) was added. Stirred at RT for 2 h, added EtOAc (250 mL) and then washed with water (2×100 mL), 4% MgSO4 (2×75 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford the crude product as yellow oil. Purified by chromatography using EtOAc/petroleum ether (40-60)(1:20) as the eluent, affording the title compound as an colourless, clear oil.

後処理

  1. washwashed with water (2×100 mL), 4% MgSO4 (2×75 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product as yellow oil
  6. customPurified by chromatography

出典と根拠

ORDレコード
ord-53b0c7c024f14f7a94e90f85814a9069
出典データセット
uspto-grants-2011_07
特許番号
US07977387B2

関連ノート

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