Boron trifluoride etherate → HCID 21491839, compound

HRID 1731051Notes

Reaction equation

HRID 1731051 reaction equation
[CH2:1]([O:5][C:6](=[O:21])[CH:7](OC(=O)C)[NH:8][C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[CH2:2][CH2:3][CH3:4].[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[OH:30].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:5][C:6](=[O:21])[CH:7]([C:27]1[CH:26]=[C:25]([CH3:29])[C:24]([OH:30])=[C:23]([CH3:22])[CH:28]=1)[NH:8][C:9]([O:11][CH2:12][C:13]([Cl:14])([Cl:15])[Cl:16])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 113352,6-DimethylphenolHCID 20312432HCID 20312432, compound

Product 1

HCID 21491839HCID 21491839, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneCatalyst

Procedure

A solution of 1.8 g. (6 mmol.) of N-(β,β,β-trichloroethoxycarbonyl)-2-acetoxyglycine n-butyl ester and 1.2 g. (10 mmol.) of 2,6-dimethylphenol in 20 ml. of methylene chloride containing 3 drops of boron trifluoride etherate was stirred at 25° for 3 hours. The reaction mixture was concentrated in vacuo, 5 ml. of 2:1 hexanemethylene chloride was added and the resulting solution was chromatographed on silica gel. Elution with 2:1 hexanemethylene chloride then with methylene chloride containing increasing amounts of ethyl acetate gave the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, 5 ml
  2. additionof 2:1 hexanemethylene chloride was added
  3. customthe resulting solution was chromatographed on silica gel
  4. washElution with 2:1 hexanemethylene chloride
  5. temperaturewith methylene chloride containing increasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-4793f3b620b9411a9ca56e7559460f36
Source dataset
uspto-grants-1976_11
Patent number
US03994954

Reaction notes

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