Ethyl Acetate → HCID 19763643, compound

HRID 1762722Notes

Reaction equation

HRID 1762722 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[O:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OCC)(=O)C>C(Cl)Cl>[F:1][C:2]([F:13])([F:14])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 36276076-(Trifluoroacetamido)-1-hexanol

Product 1

HCID 19763643HCID 19763643, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To 2.1 gm (10.1 mmole) of the 6-trifluroacetamido-1-hexanol in 40 ml of methylene chloride was added 3 gm (10.64 mmole) of pyridinium dichromate and 4.4 gm of 3 Angstrom molecular sieves, and the reaction was allowed to proceed with stirring for 3 hours at 23° C. After addition of 250 ml of ethyl acetate, the reaction mixture was filtered through a small bed of silica gel 60 and concentrated in vacuo. Flash chromatography using 50% (v/v) ethyl acetate in hexane afforded 1.48 gms (70%) of 6-trifluroacetamido-1-hexanal. ##STR17##

Workup

  1. filtrationthe reaction mixture was filtered through a small bed of silica gel 60
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-106ab3ab2a1448b9916eb0bd940cde3e
Source dataset
uspto-grants-1989_05
Patent number
US04833251

Reaction notes

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