(2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-4,4-dimethylcyclohexanone → (2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-1-(4-chlorophenyl)-4,4-dimethylcyclohexanol

HRID 1920446Notes

Reaction equation

HRID 1920446 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:7][CH2:6][C:5](=[O:8])/[C:4](=[CH:9]/[O:10][Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])/[CH2:3]1.[CH3:22][C:23]1([CH3:36])[CH2:28][CH2:27][C:26](=[O:29])/[C:25](=[CH:30]/[O:31][Si:32]([CH3:35])([CH3:34])[CH3:33])/[CH2:24]1.[Si:37]([O:44]/[CH:45]=[C:46]1/[C:47](=[O:54])[CH2:48][CH2:49][C:50]([CH3:53])([CH3:52])[CH2:51]/1)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38].[Cl:55][C:56]1[CH:61]=[CH:60][C:59]([Mg]Br)=[CH:58][CH:57]=1>>[Cl:55][C:56]1[CH:61]=[CH:60][C:59]([C:5]2([OH:8])[CH2:6][CH2:7][C:2]([CH3:1])([CH3:21])[CH2:3]/[C:4]/2=[CH:9]\[O:10][Si:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:18]([CH3:20])[CH3:19])=[CH:58][CH:57]=1.[Cl:55][C:56]1[CH:61]=[CH:60][C:59]([C:26]2([OH:29])[CH2:27][CH2:28][C:23]([CH3:36])([CH3:22])[CH2:24]/[C:25]/2=[CH:30]\[O:31][Si:32]([CH3:34])([CH3:33])[CH3:35])=[CH:58][CH:57]=1.[Si:37]([O:44]/[CH:45]=[C:46]1/[C:47]([C:59]2[CH:60]=[CH:61][C:56]([Cl:55])=[CH:57][CH:58]=2)([OH:54])[CH2:48][CH2:49][C:50]([CH3:53])([CH3:52])[CH2:51]/1)([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38]

Participants

7

Reactant 4

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)cyclohexanoneHCID 178478191HCID 178478191, compound

Product 3

HCID 67079181(2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-1-(4-chlorophenyl)-4,4-dimethylcyclohexanolHCID 67079716(2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanolHCID 67079763(2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((trimethylsilyl)oxy)methylene)cyclohexanol

Procedure

reacting 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 and 4-chlorophenyl magnesium bromide at about −10° C. to about 5° C. to provide ((2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanol, (2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((trimethylsilyl)oxy)methylene)cyclohexanol, or (2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-1-(4-chlorophenyl)-4,4-dimethylcyclohexanol; and isolating or not isolating the ((2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((triisopropylsilyl)oxy)methylene)cyclohexanol, (2E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(((trimethylsilyl)oxy)methylene)cyclohexanol, or (2E)-2-(((tert-butyl(dimethyl)silyl)oxy)methylene)-1-(4-chlorophenyl)-4,4-dimethylcyclohexanol, and

Workup

  1. customat about −10° C. to about 5° C.

Sources & evidence

ORD record
ord-503d23e86e1b4f17a2d834bb995059f0
Source dataset
uspto-grants-2012_05
Patent number
US08168784B2

Reaction notes

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