Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate → HCID 18952387、化合物

HRID 1492307ノート

反応式

HRID 1492307 の反応式
[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:19][CH:20]=[CH2:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:19][CH2:20][CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

参加物

4

反応物 1

HCID 19385705Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate

生成物 1

HCID 18952387HCID 18952387、化合物収率 80.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate (14.4 g) (obtained as described in International patent application, publication no. WO 91/11999) in methanol (280 ml) was catalytically hydrogenated over 10% palladium on carbon (2.9 g) at 3 atmospheres pressure for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:3 v/v), to give methyl 4-(t-butyldimethylsilyloxy)-3-propylbenzoate (B) (11.7 g) as an oil; NMR: 0.25(s, 6H), 0.95(t, 3H), 1.0(s, 9H), 1.5-1.7(m, 2H), 2.6(t, 2H), 3.9(s, 3H), 6.8(d, 1H), 7.8(dd, 1H), 7.8(s, 1H).

後処理

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated by evaporation
  3. customThe residue was purified by flash chromatography
  4. washeluting with ethyl acetate/hexane (1:3 v/v)

出典と根拠

ORDレコード
ord-86da75fd7f49456cb8a013750c1e6a8a
出典データセット
uspto-grants-1994_12
特許番号
US05373015

反応ノート

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