Nitrogen → 1-(3-[Tert-butyl(diphenyl)silyl]oxycyclobutyl)ethanone

HRID 1692945노트

반응식

HRID 1692945 반응식
[Si:1]([O:18][CH:19]1[CH2:22][CH:21]([C:23](N(OC)C)=[O:24])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][Mg]I.N#N>CCOCC>[Si:1]([O:18][CH:19]1[CH2:20][CH:21]([C:23](=[O:24])[CH3:29])[CH2:22]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 947NitrogenHCID 866343493-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylcyclobutanecarboxamideHCID 178418373HCID 178418373, 화합물

생성물 1

HCID 668242881-(3-[Tert-butyl(diphenyl)silyl]oxycyclobutyl)ethanone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 3-[tert-butyl(diphenyl)silyl]oxy-N-methoxy-N-methylcyclobutanecarboxamide (0.7 g, 0.002 mol) in ether (10 mL) was added into 3.0 M of methylmagnesium iodide in ether (3 mL) slowly under N2. The reaction was stirred and heated to reflux for 2 h. The mixture was quenched with ice and the ether layer separated. The aq. layer was acidified with 1N HCl and extracted several times with ether. The organic layers were combined, dried over MgSO4, concentrated and purified with Combiflash (silica gel, 0-30% EtOAc/Hex) to give the desired product (0.6 g) as colorless oil. LCMS calculated for C22H29O2Si(M+H)+: 353.2; Found: 353.3.

후처리

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. customThe mixture was quenched with ice
  4. customthe ether layer separated
  5. extractionextracted several times with ether
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified with Combiflash (silica gel, 0-30% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-2336e435736d4b5cb51f73a04011942f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158616B2

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