2-[(Dimethylamino)methylidene]cyclohexane-1,3-dione → 3-(Tert-butyldiphenylsilyloxy)propanenitrile

HRID 747053Notes

Reaction equation

HRID 747053 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21](N)=[NH:22])([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.CN(C=C1C(=O)CCCC1=O)C>CCO>[C:14]([Si:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[O:18][CH2:19][CH2:20][C:21]#[N:22])([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dioneHCID 588414073-(Tert-butyldiphenylsilyloxy)propanamidine

Product 1

HCID 108287163-(Tert-butyldiphenylsilyloxy)propanenitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A Solution of 3-(tert-butyldiphenylsilyloxy) propanamidine (25 g, 77 mmol) and 2-((dimethylamino)methylene)cyclohexane-1,3-dione (12.8 g, 77 mmol) in 400 mL of dry EtOH was heated at 80° C. for 3 h. After cooling to room temperature, the solvent was evaporated. Flash chromatography (SiO2, EtOAc/hexane=1:1) gave the title compound as a white solid.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cfe6f594925743bfbed42869acc3bf0e
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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