Sodium 2-methyl-2-propanethiolate → 3-tert-Butylsulfanyl-6,6-dimethyl-1-(1H-pyrazol-3-yl)-6,7-dihydro-5H-benzo[c]thiophen-4-one

HRID 1385287Notes

Reaction equation

HRID 1385287 reaction equation
C([N:4]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11](S(C)=O)=[C:12]3[C:17](=[O:18])[CH2:16][C:15]([CH3:20])([CH3:19])[CH2:14][C:13]=23)=[N:5]1)(=O)C.[CH3:24][C:25]([S-:28])([CH3:27])[CH3:26].[Na+]>C1COCC1>[CH3:19][C:15]1([CH3:20])[CH2:14][C:13]2=[C:9]([C:6]3[CH:7]=[CH:8][NH:4][N:5]=3)[S:10][C:11]([S:28][C:25]([CH3:27])([CH3:26])[CH3:24])=[C:12]2[C:17](=[O:18])[CH2:16]1

Participants

4

Reactant 2

HCID 5147913Sodium 2-methyl-2-propanethiolate2×HCID 211845311-(1-Acetylpyrazol-3-yl)-6,6-dimethyl-3-methanesulphinyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one

Product 1

HCID 1784268003-tert-Butylsulfanyl-6,6-dimethyl-1-(1H-pyrazol-3-yl)-6,7-dihydro-5H-benzo[c]thiophen-4-oneYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(1-acetylpyrazol-3-yl)-6,6-dimethyl-3-methanesulphinyl-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (73 mg, 0.21 mmol) in THF (7 mL) was added sodium 2-methyl-2-propanethiolate (47 mg, 0.42 mmol). After 90 min more sodium 2-methyl-2-propanethiolate (15 mg, 0.14 mmol) was added, and after a further 30 min the mixture was partitioned between EtOAc (15 mL) and water (10 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol:EtOAc (1:1), to give the title compound (34 mg, 48%) as a yellow solid. mp 220-222° C.

Workup

  1. customafter a further 30 min the mixture was partitioned between EtOAc (15 mL) and water (10 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with petrol:EtOAc (1:1)

Sources & evidence

ORD record
ord-9df5b5ef2cb24dc295376e85d503e1ad
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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