Dimethyl Sulfide → 2-Ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester

HRID 479197노트

반응식

HRID 479197 반응식
CSC.B(F)(F)F.CCOCC.[CH3:13][O:14][C:15](=[O:38])[CH:16]([O:35][CH2:36][CH3:37])[CH2:17][C:18]1[C:26]2[O:25][CH:24]=[CH:23][C:22]=2[C:21]([O:27]CC2C=CC=CC=2)=[CH:20][CH:19]=1>ClCCl>[CH3:13][O:14][C:15](=[O:38])[CH:16]([O:35][CH2:36][CH3:37])[CH2:17][C:18]1[C:26]2[O:25][CH:24]=[CH:23][C:22]=2[C:21]([OH:27])=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 68617324[Rac]-3-(4-benzyloxy-benzofuran-7-yl)-2-ethoxy-propionic acid methyl ester

생성물 1

HCID 686172122-Ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dimethyl sulfide (4.4 ml, 60 mmol) and boron trifluoride diethyl etherate (46% purity, 3.3 ml, 12 mmol) were added to a ice cold solution of [rac]-3-(4-benzyloxy-benzofuran-7-yl)-2-ethoxy-propionic acid methyl ester (0.85 g, 2.4 mmol) in dichloromethane (25 ml) under an argon atmosphere. The mixture was stirred for 6 h at ambient temperature, poured into ice water and extracted three times with dichloromethane. The combined extract was washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a brown oil which was purified by column chromatography (silica gel, hexane/AcOEt=4/1) to give 0.45 g (1.7 mmol, 71%) of the title compound as light yellow oil.

후처리

  1. extractionextracted three times with dichloromethane
  2. extractionThe combined extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customgave a brown oil which
  7. customwas purified by column chromatography (silica gel, hexane/AcOEt=4/1)

출처 및 근거

ORD 기록
ord-cdfa8301c64c4f9593e459fa1c82cb5d
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642389B2

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