tert-Butyl mercaptan → HCID 14980527, compound

HRID 1590089Notes

Reaction equation

HRID 1590089 reaction equation
Cl[CH2:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8].[CH3:14][C:15]([SH:18])([CH3:17])[CH3:16].CCN(CC)CC>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C1COCC1>[C:15]([S:18][CH2:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7]([O:9][CH3:10])=[O:8])([CH3:17])([CH3:16])[CH3:14]

Participants

6

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 8471TriethylamineHCID 14980526HCID 14980526, compound

Product 1

HCID 14980527HCID 14980527, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the α-chloroketone (1 eq) from Step 5, 2-methyl-2-propanethiol (1.2 eq), Et3N (1.5 eq) and n-Bu4NBr (catalytic amount) in THF at room temperature under nitrogen was stirred for 24 hours. The mixture was filtered and the solvent removed in vacuo. Chromatography of the oily residue on silica gel (hexane/EtOAc 10:1) provide the title compound as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b0189d5e71c24f9787f61d085d499406
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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