tert-Butyl mercaptan → HCID 70855406, compound

HRID 591057Notes

Reaction equation

HRID 591057 reaction equation
Br[CH:2]([C:7]1[C:11]([C:12]2[CH:13]=[CH:14][C:15]3[O:20][CH2:19][CH2:18][CH2:17][C:16]=3[CH:21]=2)=[C:10]([CH3:22])[S:9][C:8]=1[CH3:23])[C:3]([O:5][CH3:6])=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:30][C:31]([SH:34])([CH3:33])[CH3:32]>CN(C)C=O>[C:31]([S:34][CH:2]([C:7]1[C:11]([C:12]2[CH:13]=[CH:14][C:15]3[O:20][CH2:19][CH2:18][CH2:17][C:16]=3[CH:21]=2)=[C:10]([CH3:22])[S:9][C:8]=1[CH3:23])[C:3]([O:5][CH3:6])=[O:4])([CH3:33])([CH3:32])[CH3:30]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 10796Cesium carbonateHCID 86717844HCID 86717844, compound

Product 1

HCID 70855406HCID 70855406, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-bromo-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2,5-dimethylthiophen-3-yl]acetate (32a) (50 mg, 0.126 mmol), cesium carbonate (82 mg, 0.253 mmol) and 2-methyl-2-propanethiol (23 mg, 0.253 mmol) in N,N-dimethylformamide (2 mL) was stirred at room temperature for 5 hours. The reaction mixture was quenched with water (6 mL) and extracted with ethyl acetate (4×5 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20) to provide the desired thio-ether (32b) (28 mg, 0.07 mmol, 55%) as a clear yellow oil.

Workup

  1. customThe reaction mixture was quenched with water (6 mL)
  2. extractionextracted with ethyl acetate (4×5 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-2c761b446c904ae28852378a9a9281cd
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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