Potassium Carbonate → 6-Benzyloxy-benzofuran-2-carboxylic acid tert-butyl ester

HRID 250275

反応式

HRID 250275 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:24]([O:28][C:29](=[O:32])[CH2:30]Br)([CH3:27])([CH3:26])[CH3:25].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[C:24]([O:28][C:29]([C:30]1[O:17][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:16]=[CH:15][C:12]=2[CH:13]=1)=[O:32])([CH3:27])([CH3:26])[CH3:25]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

生成物 1

HCID 672718976-Benzyloxy-benzofuran-2-carboxylic acid tert-butyl ester収率 72%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

To a solution of 4-benzyloxy-2-hydroxy-benzaldehyde (5.56 g, 24.4 mmol) in DMF (20 mL) is added K2CO3 (6.73 g, 48.8 mmol), bromo-acetic acid tert-butyl ester (4.75 g, 24.4 mmol), and DBU (1.0 mL). The mixture is heated to 140° C. for 2 hours and cooled to room temperature. The mixture is quenched with water (200 mL) and extracted with EtOAc (100 mL). The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue is purified by silica gel chromatography cluting with 15% EtOAc/Hexanes to provide the title compound (5.68 g, 72%). LC-ES/MS m/e 269.0 (acid, M+1)

後処理

  1. temperaturecooled to room temperature
  2. customThe mixture is quenched with water (200 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-3ecd02b481cc45819b06dbeb464c34e2
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

関連ノート

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