Hexane → Dimethyl 3-phenylthiocyclobutane-1,2-dicarboxylate

HRID 5975

Reaction equation

HRID 5975 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])/[CH:2]=[CH:3]\[C:4]([O:6][CH3:7])=O.C([S:13]C1C=CC=CC=1)=C.[Cl-].[Cl-].[CH2:22]([Al+2])[CH3:23].[CH3:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>ClCCCl.C(Cl)Cl>[C:27]1([CH:22]2[CH2:23][CH:3]([C:4]([O:6][CH3:7])=[S:13])[CH:2]2[C:1]([O:9][CH3:10])=[O:8])[CH:26]=[CH:25][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 74572Phenyl Vinyl SulfideHCID 5271565Dimethyl maleateHCID 16686341Ethyl aluminium dichloride

Product 1

HCID 86746186Dimethyl 3-phenylthiocyclobutane-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of dimethyl maleate (0.50 mL, 4 mmol) and phenyl vinyl sulfide (0.52 mL, 4 mmol) in 17 mL of 1,2-dichloroethane under nitrogen atmosphere, was added 1 equivalent (4 mL of a 1 M solution in hexane) of ethylaluminum dichloride. The resultant solution was heated at 85° C. for 18 h and then diluted with 75 mL of methylene chloride. The methylene chloride solution was washed three times with saturated aqueous ammonium chloride and once with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give 0.98 g of the title compound; EI-MS, m/e (rel intensity): 280 (M+, 14), 136 (100).

Workup

  1. washThe methylene chloride solution was washed three times with saturated aqueous ammonium chloride
  2. dry with materialonce with brine, dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cfd97c6b760d447ab41eb374f30d7b03
Source dataset
uspto-grants-1993_09
Patent number
US05246931

Linked notes

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