Ethanol → HCID 19879355, compound

HRID 1885603Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:10]=[C:11]([CH2:19][CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(O)C>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH:11]([CH2:19][CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 3,4-dichlorobenzenethiol (0.20 ml), di-tert-butyl 2-methyleneadipate (350 mg), ethanol (2 ml), and triton B (40% methanol solution, 2 drops) was stirred at 170° C. in a sealed tube for 17 hours. After the reaction mixture was concentrated in vacuo, the resulting residue was dissolved in chloroform, washed with a 0.5% sodium hydroxide solution, water and a saturated sodium chloride solution respectively, and dried over MgSO4. The solvent was evaporated at reduced pressure, and the residue was purified by flash column chromatography on silica by eluting with diethyl ether/hexane (1:10) to give 430 mg of di-tert-butyl 2-(3,4-dichlorophenylthiomethyl)adipate as an oil.

Workup

concentrationAfter the reaction mixture was concentrated in vacuo
dissolutionthe resulting residue was dissolved in chloroform
washwashed with a 0.5% sodium hydroxide solution, water
dry with materiala saturated sodium chloride solution respectively, and dried over MgSO4
customThe solvent was evaporated at reduced pressure
customthe residue was purified by flash column chromatography on silica
washby eluting with diethyl ether/hexane (1:10)

Sources & evidence

ORD record: ord-b6571d268bcf43e5ac4346b1e583fbef
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145869

Reaction notes

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