Water → 3-[3-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-benzyl]-benzoic acid methyl ester

HRID 1161032노트

반응식

HRID 1161032 반응식
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([SH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[CH3:15][O:16][C:17](=[O:33])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]I)[CH:26]=2)[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(=O)CC>[CH3:15][O:16][C:17](=[O:33])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][S:11][C:6]3[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=3[CH2:8][CH2:9][CH3:10])[CH:26]=2)[CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-oneHCID 574383053-(3-Iodomethyl-benzyl)-benzoic acid methyl ester

생성물 1

HCID 666995593-[3-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-benzyl]-benzoic acid methyl ester수율 85%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

Stir a mixture of 1-(2-Hydroxy-4-mercapto-3-propyl-phenyl)-ethanone (132 mg, 0.63 mmol), 3-(3-Iodomethyl-benzyl)-benzoic acid methyl ester (230 mg, 0.63 mmol), and cesium carbonate (410 mg, 1.26 mmol) in 2-butanone (6 ml) at room temperature under argon for 20 hours. Pour the mixture into water (60 ml) and extract with ethyl acetate (2×30 ml). Combine the organic extracts and wash with water, brine, then dry over sodium sulfate, filter and concentrate. Purify the crude product via silica chromatography eluting with 1:4 ethyl acetate:hexanes to give the title compound (240 mg, 85%). MS (m/z) 447 (M−H).

후처리

  1. extractionextract with ethyl acetate (2×30 ml)
  2. washCombine the organic extracts and wash with water, brine
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude product via silica chromatography
  7. washeluting with 1:4 ethyl acetate

출처 및 근거

ORD 기록
ord-9d439703520a4617845e8cd92f9a133c
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816523B2

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