Benzyl mercaptan → HCID 67313980, compound

HRID 1011492Notes

Reaction equation

HRID 1011492 reaction equation
[C:1]1([CH2:7][SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH:15]1([C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][C:24]=2F)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[NH4+].[Cl-]>C1COCC1>[CH:15]1([C:21]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][C:28]=2[S:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67219586HCID 67219586, compound

Product 1

HCID 67313980HCID 67313980, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of phenylmethanethiol (2.35 ml, 20 mmoles) in THF (10 ml) was slowly added to a mixture of potassium tert-butoxide (2.24 g, 20 mmoles) in THF (80 ml) under N2 at room temperature. The mixture was stirred for 15 min at room temperature and cyclohexyl (4-benzyloxy-2-fluorophenyl)methanone (6.5 g, 20 mmoles) in THF (10 ml) was slowly added. The mixture was heated for 2 h at 50° C. and poured into an aqueous solution of NH4Cl, extracted with ethyl acetate, dried over Na2SO4 and concentrated under vacuum. The crude product was purified by flash chromatography (Heptane/AcOEt 90/10 with 0.1% TEA) to give cyclohexyl (4-benzyloxy-2-benzylthiophenyl)methanone (8.3 g, 100%).

Workup

  1. temperatureThe mixture was heated for 2 h at 50° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by flash chromatography (Heptane/AcOEt 90/10 with 0.1% TEA)

Sources & evidence

ORD record
ord-41464898ac4844fdb35dcaa4dd0dd8b7
Source dataset
uspto-grants-2011_07
Patent number
US07977364B2

Reaction notes

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