HCID 86675581、化合物 → HCID 71183845、化合物

HRID 1422598ノート

反応式

HRID 1422598 の反応式
[N+](=[C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])=[N-]>ClCCl.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.[Rh+2].[Rh+2]>[N+:16]([C:12]1[CH:11]=[C:10]([C:3]23[CH2:9][CH:8]2[CH2:7][O:6][C:4]3=[O:5])[CH:15]=[CH:14][CH:13]=1)([O-:18])=[O:17]

参加物

4

反応物 1

HCID 86675581HCID 86675581、化合物

生成物 1

HCID 71183845HCID 71183845、化合物収率 91.1%

試薬・触媒・溶媒 2

HCID 11621934Rhodium(II) octanoate dimer触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of commercially available rhodium(II) octanoate dimer (Rh2(C7H16CO2)4) CAS-no. [73482-96-9] (440 mg, 565 μmol, Eq: 0.00941) in dichloromethane (180 ml) at 50° C. was added a solution of allyl 2-diazo-2-(3-nitrophenyl)acetate (intermediate B4a) (14.85 g, 60.1 mmol, Eq: 1.00) in dichloromethane (38 ml) via syringe pump within 18 h. Refluxing was continued for 30 min, the solvent was evaporated and the crude material was purified by flash chromatography (silica gel, 70 g, 0% to 100% EtOAc in heptane) to give (1SR,5RS)-1-(3-nitrophenyl)-3-oxabicyclo[3.1.0]hexan-2-one (12 g, 54.7 mmol, 91.1% yield) as a light brown solid. [cf. Adv. Synth. Catal. 2001, 343, 299 for an enantioselective version of this reaction]. MS (ISP): m/z=237.1 [(M+NH4)+].

後処理

  1. temperatureRefluxing
  2. customthe solvent was evaporated
  3. customthe crude material was purified by flash chromatography (silica gel, 70 g, 0% to 100% EtOAc in heptane)

出典と根拠

ORDレコード
ord-1e705b2ec02c4285bdc0f39540511412
出典データセット
uspto-grants-2015_01
特許番号
US08927535B2

反応ノート

読み込み中…