Benzophenone → Benzyl acetate

HRID 2109873Notes

Reaction equation

HRID 2109873 reaction equation
[C:1]1([O:7][Si](CC2C=CC=CC=2C2C3C(=CC=CC=3)C=CC=2)(C)C)CCCC[CH:2]=1.C1(=O)CCCCC1.C([N-]C(C)C)(C)C.[Li+].C1(C2C=CC=CC=2C[Si](Cl)(C)C)C2C(=CC=CC=2)C=CC=1.[H][H].[C:66]([C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)(=[O:73])C1C=CC=CC=1>CC(C)=O>[C:1]([O:73][CH2:66][C:74]1[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=1)(=[O:7])[CH3:2]

Participants

8

Reactant 6

HCID 3102BenzophenoneHCID 7967Cyclohexanone2×HCID 2724682Lithium diisopropylamideHCID 23110755HCID 23110755, compoundHCID 68843896HCID 68843896, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 8785Benzyl acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

For example, 1-cyclohexenyloxy-[((1-naphthyl)phenyl)methyl]dimethylsilane, which is a silyl enol ether form of cyclohexanone, may be formed by treating cyclohexanone with lithium diisopropylamide at low temperature (e.g. −78° C.) so as to generate a lithium enolate, and capturing this with [((1-naphthyl)phenyl)methyl]dimethylsilyl chloride. By the same method, a ketone having an active hydrogen such as acetone or benzophenone may be derivatized to the corresponding silyl enol ether. Furthermore, a silyl ketene acetal form of benzyl acetate may be formed by treating benzyl acetate with lithium diisopropylamide at low temperature (e.g. −78° C.) so as to generate a lithium enolate, and capturing this with [((1-naphthyl)phenyl)methyl]dimethylsilyl chloride. By the same method, a carboxylic acid ester having an active hydrogen may be derivatized to the corresponding silyl ketene acetal.

Workup

  1. custommay be formed

Sources & evidence

ORD record
ord-4e82fe5138364975a0539348717d7d59
Source dataset
uspto-grants-2009_04
Patent number
US07517828B2

Reaction notes

Loading…