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

HRID 1966166ノート

反応式

HRID 1966166 の反応式
[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

参加物

5

反応物 3

HCID 947NitrogenHCID 866343493-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylcyclobutanecarboxamideHCID 178418373HCID 178418373、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-db5d2869f40d411098eda4a003fe5fdb
出典データセット
uspto-grants-2013_04
特許番号
US08420629B2

反応ノート

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