Hydrochloric Acid → 2-(4-Benzyloxybenzyl)-2-phenoxy-3-(2,2,2-trifluoroacetoxy)hexanoic acid ethyl ester

HRID 348373Notes

Reaction equation

HRID 348373 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[C:5]([CH:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)O)([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:2].N1C=CC=CC=1.[F:40][C:41]([F:52])([F:51])[C:42]([O:44]C(=O)C(F)(F)F)=[O:43].Cl>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:33])[C:5]([CH2:17][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:6]([O:44][C:42](=[O:43])[C:41]([F:52])([F:51])[F:40])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 693540782-[(4-Benzyloxyphenyl)-hydroxymethyl]-2-phenoxy-hexanoic acid ethyl ester

Product 1

HCID 693532492-(4-Benzyloxybenzyl)-2-phenoxy-3-(2,2,2-trifluoroacetoxy)hexanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(4-Benzyloxyphenyl)-hydroxymethyl]-2-phenoxy-hexanoic acid ethyl ester (13.4 mmol) in anhydrous CH2Cl2 (100 mL) and pyridine (134 mmol) was cooled to 0° C. and treated with trifluoroacetic anhydride (26.9 mmol). The mixture was stirred for 2 h and gradually warmed to ambient temperature. An aqueous solution of 1N HCl (150 mL) was added and the mixture was stirred vigorously. The solution was partitioned and the organic layer was washed twice with water and brine, dried over Na2SO4, and concentrated in vacuo to produce 2-(4-benzyloxybenzyl)-2-phenoxy-3-(2,2,2-trifluoroacetoxy)hexanoic acid ethyl ester as an oil.

Workup

  1. stirringthe mixture was stirred vigorously
  2. customThe solution was partitioned
  3. washthe organic layer was washed twice with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35e8568ccd21446f894776134b4d002c
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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