Water → methyl (Z)-4-benzyloxy-3-(1-methyl-propenyl)-benzoate

HRID 424044ノート

反応式

HRID 424044 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:26]/[C:27](/B(O)O)=[CH:28]/[CH3:29].O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1/[C:27](/[CH3:26])=[CH:28]\[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11389361(E)-But-2-EN-2-ylboronic acidHCID 23111814Methyl 4-(benzyloxy)-3-bromobenzoate

生成物 1

HCID 57830180methyl (Z)-4-benzyloxy-3-(1-methyl-propenyl)-benzoate収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 4-benzyloxy-3-bromobenzoate (1.61 g, 5.0 mmol), caesium carbonate (4.89 g, 15.0 mmol), (E)-2-buten-2-yl boronic acid (600 mg, 6.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocenyl]palladium (II) chloride (204 mg, 0.25 mmol) were dissolved in anhydrous tetrahydrofuran (100 ml), water (10 ml) was added and the mixture was stirred and held at reflux under an atmosphere of nitrogen for 16 hours. Upon cooling the solvent was removed in vacuo and the mixture partitioned between dichloromethane and water. The organic layer was separated, the solvent removed in vacuo and the residue subjected to column chromatography on silica. Elution with 5% ethyl acetate in petroleum ether afforded methyl (Z)-4-benzyloxy-3-(1-methyl-propenyl)-benzoate (600 mg, 41%) as a colourless solid. 1H NMR (DMSO-d6) 7.88 (1H, dd), 7.59 (1H, d), 7.40 (4H, m), 7.34 (1H, m), 7.23 (1H, d), 5.57 (1H, q), 5.21 (2H, s), 3.82 (3H, s), 1.94 (3H, s), 1.38 (3H, d).

後処理

  1. temperatureat reflux under an atmosphere of nitrogen for 16 hours
  2. temperatureUpon cooling the solvent
  3. customwas removed in vacuo
  4. customthe mixture partitioned between dichloromethane and water
  5. customThe organic layer was separated
  6. customthe solvent removed in vacuo
  7. washElution with 5% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-fe05faf9741b419d96320e523e8eb000
出典データセット
uspto-grants-2012_01
特許番号
US08101648B2

反応ノート

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