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

HRID 1717719Notes

Reaction equation

HRID 1717719 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-519e0cf76b6e4e9f8971a6e77950a0fb
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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