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

HRID 1966166Notes

Reaction equation

HRID 1966166 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-db5d2869f40d411098eda4a003fe5fdb
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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