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

HRID 465768

반응식

HRID 465768 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-318cfed1a7c845efb279bf3e11736f46
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153352

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