Anisole → HCID 20312434, compound

HRID 1731050Notes

Reaction equation

HRID 1731050 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].[C:22]1([O:28][CH3:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:5][C:6](=[O:21])[CH:7]([C:25]1[CH:26]=[CH:27][C:22]([O:28][CH3:29])=[CH:23][CH:24]=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 7519AnisoleHCID 8000Boron trifluoride etherateHCID 20312432HCID 20312432, compound

Product 1

HCID 20312434HCID 20312434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneCatalyst

Procedure

A solution of 0.91 g. (3.0 mmol.) of N-(β,β,β-trichloroethoxycarbonyl)-2-acetoxyglycine n-butyl ester and 0.3 g. (2.8 mmol.) of anisole in 20 ml. of methylene chloride containing two drops of boron trifluoride etherate was maintained at 25° for 5 hours. The solvent was then evaporated in vacuo and 2:1 hexane-methylene chloride was added. Chromatography on silica gel with methylene chloride containing increasing amounts of ethyl acetate gave the title compound.

Workup

  1. customThe solvent was then evaporated in vacuo and 2:1 hexane-methylene chloride
  2. additionwas added
  3. temperatureChromatography on silica gel with methylene chloride containing increasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-3aed9dc5bb824345a9e246b392dea4ca
Source dataset
uspto-grants-1976_11
Patent number
US03994954

Reaction notes

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