p-Toluenesulfonic acid → 3-[(Butylsulfanyl)methylidene]oxolan-2-one

HRID 973944노트

반응식

HRID 973944 반응식
CN([CH:4]=[C:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10])C.[CH2:11]([SH:15])[CH2:12][CH2:13][CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:11]([S:15][CH:4]=[C:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10])[CH2:12][CH2:13][CH3:14]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 8012ButanethiolHCID 3045663-Dimethylaminomethylenedihydrofuran-2-one

생성물 1

HCID 539081313-[(Butylsulfanyl)methylidene]oxolan-2-one

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of γ-butyrolactone (1 mol) and tris(dimethylamino)methane (1.5 mol) is stirred under dry nitrogen at 75° C. for 2 days to give 3-[(dimethylamino)methylene]dihydro-2(3H)-furanone. A solution containing 3-[(dimethylamino)methylene]dihydro-2(3H)-furanone (1 mol), n-butanethiol (1.1 mol) and para-toluenesulfonic acid (1 mol) in benzene is heated at reflux overnight to give upon aqueous work-up 3-[(butylthio)methylene]dihydro-2(3H)-furanone. After a solution of 3-[(butylthio)methylene]dihydro-2(3H)-furanone (1 mol) in anhydrous diethyl ether is added to a solution of lithium di-n-butylcuprate (1.1 mol) in diethyl ether at -78° C., the resulting mixture is stirred at -78° C. for an additional 0.5 hours and then quenched with methanol. Work-up affords 3-ethylidenedihydro-2(3H)-furanone. Freshly prepared W-2 Raney nickel (about 3 parts) is deactivated by refluxing in benzene for 1 hour, whereupon 3-ethylidenedihydro-2(3H)-furanone is added and the mixture is heated at reflux under nitrogen for 24-48 hours; the reaction is monitored by thin layer chromatography. After complete washing of the Raney nickel with hot benzene, the title compound is obtained.

후처리

  1. temperatureis heated
  2. temperatureat reflux overnight

출처 및 근거

ORD 기록
ord-baf41da3cff24887bb21ecdc18ab511c
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05066663

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