Cyclohexanone → (3R,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]4-methylenecyclohexanone

HRID 1817982Notes

Reaction equation

HRID 1817982 reaction equation
[Si:1]([O:8][C@H:9]1[C:14](=[CH2:15])[C@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:12][CH:11]([OH:24])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].C1(=O)CCCCC1>C1(C)C=CC=CC=1>[Si:1]([O:8][C@H:9]1[C:14](=[CH2:15])[C@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:12][C:11](=[O:24])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 11143Aluminum isopropoxideHCID 10248733HCID 10248733, compound2×

Product 1

HCID 10690562(3R,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]4-methylenecyclohexanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

For example, a solution of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-methylenecyclohexanol (compound 9) in toluene is made to react with aluminum isopropoxide and cyclohexanone to produce (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-4-methylenecyclohexanone (compound 10).

Sources & evidence

ORD record
ord-c6a0283300f74d42ba0635c2f00ef0f5
Source dataset
uspto-grants-2009_10
Patent number
US07598408B2

Reaction notes

Loading…