Dimethyl Sulfide → HCID 67566324, compound

HRID 1452388Notes

Reaction equation

HRID 1452388 reaction equation
[Cl:1]N1C(=O)CCC1=O.CSC.[C:12]([O:15][C:16]1[C:17]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:18][C:19]2[O:23][C:22]([CH2:25][CH2:26]/[CH:27]=[C:28](\[CH3:31])/[CH2:29]O)([CH3:24])[CH2:21][C:20]=2[C:32]=1[C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:14])[CH3:13]>ClCCl>[C:12]([O:15][C:16]1[C:17]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:18][C:19]2[O:23][C:22]([CH2:25][CH2:26]/[CH:27]=[C:28](\[CH3:31])/[CH2:29][Cl:1])([CH3:24])[CH2:21][C:20]=2[C:32]=1[C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 69677214HCID 69677214, compound

Product 1

HCID 67566324HCID 67566324, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

N-Chlorosuccinimide (150 mg) was suspended in dichloromethane (4 ml). After adding dimethyl sulfide (0.1 ml) dropwise at -5° C., the suspension was stirred for 15 min. Subsequently, a solution of 5-acetoxy-4,6-di-tert-butyl-2-(5-hydroxy-4-methyl-3(E)-pentenyl)-2-methyl-2,3-dihydrobenzofuran (0.4 g) in dichloromethane (1 ml) was added dropwise and the resulting mixture was stirred at -5° C. for 90 min. After the end of the reaction, dichloromethane was distilled off under reduced pressure and the concentrate was purified by silica gel chromatography (25% ethyl acetate in n-hexane) to afford 5-acetoxy-2-(5-chloro-4-methyl-3(E)-pentenyl)-4,6-di-tert-butyl-2-methyl-2,3-dihydrobenzofuran [0.3 g (yield, 70%)] as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred at -5° C. for 90 min
  2. distillationwas distilled off under reduced pressure
  3. customthe concentrate was purified by silica gel chromatography (25% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-fe0c7759f9fa40a6a9fb8c80954fe7c5
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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