Methanol → 4-(5-Methoxy-tetrahydro-furan-3-yl)-benzoic Acid Ethyl Ester

HRID 8199

反応式

HRID 8199 の反応式
N([O-])=O.[Na+].N[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1.F[B-](F)(F)F.[H+].[O:23]1[CH2:27][CH:26]=[CH:25][CH2:24]1.[CH3:28][OH:29]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:13]([O:12][C:10](=[O:11])[C:9]1[CH:15]=[CH:16][C:6]([CH:25]2[CH2:26][CH:27]([O:29][CH3:28])[O:23][CH2:24]2)=[CH:7][CH:8]=1)[CH3:14]

参加物

8

反応物 5

HCID 887MethanolHCID 2337BenzocaineHCID 155702,5-DihydrofuranHCID 28118Tetrafluoroboric acidHCID 23668193Sodium Nitrite

生成物 1

HCID 693653004-(5-Methoxy-tetrahydro-furan-3-yl)-benzoic Acid Ethyl Ester

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

実験手順

A solution of sodium nitrite (1.67 g, 24.2 mmol) in water (14 mL) is added dropwise to an ice cold mixture of ethyl 4-aminobenzoate (4.0 g, 24.2 mmol) and tetrafluoroboric acid (7.8 mL, 48%, 59.78 mmol) and stirred for 30 min. Methanol (28.5 mL), 2,5-dihydrofuran (3.66 mL, 48.4 mmol) and palladium(II) acetate (70 mg, 0.31 mmol) are added and the mixture refluxed for 30 min. The mixture is filtered through Celite® pad and the filtrate diluted with dichloromethane (100 mL). The organic layer is separated and concentrated in vacuo. The residue is chromatographed on SiO2 (10% ethyl acetate/hexanes) to yield the title compound, 2.45 g (42%), as a white solid.

後処理

  1. temperaturethe mixture refluxed for 30 min
  2. filtrationThe mixture is filtered through Celite® pad
  3. additionthe filtrate diluted with dichloromethane (100 mL)
  4. customThe organic layer is separated
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on SiO2 (10% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-e7582e27591542cc9b1ae12d23cd68f8
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

関連ノート

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