tert-Butyldimethylsilyl chloride → Methyl 2-(tert-butyldimethylsilyloxy)-6-methylbenzoate

HRID 59677

反応式

HRID 59677 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(N(CC)C(C)C)(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:13]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

参加物

6

反応物 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 584223Methyl 2-hydroxy-6-methylbenzoate

生成物 1

HCID 89705147Methyl 2-(tert-butyldimethylsilyloxy)-6-methylbenzoate収率 70.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of methyl 2-hydroxy-6-methylbenzoate (prepared according to Doehner et al, WO 01/05739, 10.0 g), tert-butyldimethylsilyl chloride (11.0 g), N,N-di-isopropylethylamine (32 mL) and DMAP (0.75 g) in DCM (400 mL) was stirred at room temperature overnight. The mixture was washed with water and brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and pentane with a gradient of 0-10% to give methyl 2-(tert-butyldimethylsilyloxy)-6-methylbenzoate (11.9 g) as an oil.

後処理

  1. washThe mixture was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and pentane with a gradient of 0-10%

出典と根拠

ORDレコード
ord-1ffebf94257d437d9795d4aab41dedd1
出典データセット
uspto-grants-2016_09
特許番号
US09440943B2

関連ノート

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