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

HRID 973944ノート

反応式

HRID 973944 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  1. temperatureis heated
  2. temperatureat reflux overnight

出典と根拠

ORDレコード
ord-baf41da3cff24887bb21ecdc18ab511c
出典データセット
uspto-grants-1991_11
特許番号
US05066663

反応ノート

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