Cornforth reagent → t-Butyldimethylsilyloxy-2,6-Dipropyl-4-formylbenzene

HRID 964455Notes

Reaction equation

HRID 964455 reaction equation
[Si:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH2:18][OH:19])=[CH:11][C:10]=1[CH2:20][CH2:21][CH3:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.C(OCC)C>[Si:1]([O:8][C:9]1[C:10]([CH2:20][CH2:21][CH3:22])=[CH:11][C:12]([CH:18]=[O:19])=[CH:13][C:14]=1[CH2:15][CH2:16][CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 19080464(4-{[tert-Butyl(dimethyl)silyl]oxy}-3,5-dipropylphenyl)methanol

Product 1

HCID 19080462t-Butyldimethylsilyloxy-2,6-Dipropyl-4-formylbenzeneYield 98.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.03 g (15.4 mmol) of t-butyl-dimethylsilyloxy-2,6-dipropyl-4-hydroxymethyl benzene in 30 mL of methylene chloride was added 8.7 g of pyridinium dichromate (PDC). The reaction mixture was stirred for 3 hours and then diluted with 300 mL of ethyl ether. The solution was then filtered through a pad of a 1:1 mixture of florisil and celite. Concentration of the filtrate gave 4.85 g of the title compound.

Workup

  1. filtrationThe solution was then filtered through a pad of a 1:1 mixture of florisil and celite

Sources & evidence

ORD record
ord-c8f350addd5b4ead9a9aa80a0bf998b2
Source dataset
uspto-grants-1998_06
Patent number
US05767310

Reaction notes

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