Anisole → HCID 20312434, compound

HRID 2420021Notes

Reaction equation

HRID 2420021 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-be687645c08848a68f80688db95286b5
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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