HCID 86675581, 화합물 → HCID 71183845, 화합물

HRID 1422598노트

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HRID 1422598 반응식
[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]

참가 물질

4

반응물 1

HCID 86675581HCID 86675581, 화합물

생성물 1

HCID 71183845HCID 71183845, 화합물수율 91.1%

시약·촉매·용매 2

HCID 11621934Rhodium(II) octanoate dimer촉매HCID 6344Dichloromethane용매2회

실험 절차

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)+].

후처리

  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)

출처 및 근거

ORD 기록
ord-1e705b2ec02c4285bdc0f39540511412
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927535B2

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