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

HRID 250275

반응식

HRID 250275 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-3ecd02b481cc45819b06dbeb464c34e2
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863302B2

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