Chlorotrimethylsilane → (2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-4,4-dimethylcyclohexanone

HRID 1920351Notes

Reaction equation

HRID 1920351 reaction equation
[OH:1]/[CH:2]=[C:3]1/[C:4](=[O:11])[CH2:5][CH2:6][C:7]([CH3:10])([CH3:9])[CH2:8]/1.[CH3:12][Si:13]([CH3:16])([CH3:15])Cl.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18].[CH:25]([Si:28]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])Cl)([CH3:27])[CH3:26]>C(N(CC)CC)C>[CH3:10][C:7]1([CH3:9])[CH2:6][CH2:5][C:4](=[O:11])/[C:3](=[CH:2]/[O:1][Si:28]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:25]([CH3:27])[CH3:26])/[CH2:8]1.[CH3:10][C:7]1([CH3:9])[CH2:6][CH2:5][C:4](=[O:11])/[C:3](=[CH:2]/[O:1][Si:13]([CH3:16])([CH3:15])[CH3:12])/[CH2:8]1.[Si:21]([O:1]/[CH:2]=[C:3]1/[C:4](=[O:11])[CH2:5][CH2:6][C:7]([CH3:9])([CH3:10])[CH2:8]/1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 139400Triisopropylsilyl chlorideHCID 12173050(2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone

Product 3

HCID 44594327(2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-4,4-dimethylcyclohexanoneHCID 44594328(2E)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanoneHCID 44594329(2E)-4,4-dimethyl-2-(((trimethylsilyl)oxy)methylene)cyclohexanone

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

reacting the (2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone, triethylamine and trimethylchlorosilane, tert-butylchlorodimethylsilane, or triisopropylchlorosilane to provide (2E)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanone, (2E)-4,4-dimethyl-2-(((trimethylsilyl)oxy)methylene)cyclohexanone, or (2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-4,4-dimethylcyclohexanone and isolating or not isolating the (2E)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanone, (2E)-4,4-dimethyl-2-(((trimethylsilyl)oxy)methylene)cyclohexanone, or (2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-4,4-dimethylcyclohexanone;

Sources & evidence

ORD record
ord-60d2515f61c94c2bb12f54692885943e
Source dataset
uspto-grants-2012_05
Patent number
US08168784B2

Reaction notes

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