HCID 13854283, compound → HCID 13854284, compound

HRID 1194037Notes

Reaction equation

HRID 1194037 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[CH2:3][OH:4].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:9]=1)[CH:3]=[O:4]

Participants

5

Reactant 2

HCID 13854283HCID 13854283, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13854284HCID 13854284, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,2-dimethyl-3-(3-benzyl-4-fluorobenzyloxy)-propan-1-ol (from the previous Example) in dichloromethane (15 cm3) was added dropwise to a stirred suspension of pyridinium chlorochromate (5.13 g) in dichloromethane (40 cm3) whilst the reaction temperature was maintained within the range 0°-5° C. When the addition was complete the mixture was allowed to warm to the ambient temperature (ca 25° C.) over a period of two hours, and left to stir for 14 hours. Diethyl ether was then added to the reaction mixture, and the whole was flushed through a plug of silica gel using diethyl ether as eluent. Evaporation of the solvent under reduced pressure gave a green oil which was subjected to column chromatography through silica gel using petroleum ether (boiling range 40°-60° C.) containing diethyl ether (10% by volume) as eluent, to give 2,2-dimethyl-3-(3-benzyl-4-fluorobenzyloxy)propan-1-al (1.40 g).

Workup

  1. temperaturewas maintained within the range 0°-5° C
  2. additionWhen the addition
  3. waitleft
  4. customthe whole was flushed through a plug of silica gel
  5. customEvaporation of the solvent under reduced pressure
  6. customgave a green oil which

Sources & evidence

ORD record
ord-2ecb972ee5ff4965a7d68320f6e763fe
Source dataset
uspto-grants-1989_03
Patent number
US04812483

Reaction notes

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