Ammonium Chloride → Ethyl 2-[5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]pentanoate

HRID 226502Notes

Reaction equation

HRID 226502 reaction equation
[Li+].[CH3:2][CH:3]([N-]C(C)C)[CH3:4].[CH2:9]([O:11][C:12](=[O:38])[CH2:13][C:14]1[CH:15]=[C:16]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[CH:17]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=1)[CH3:10].ICCC.[Cl-].[NH4+]>C1COCC1>[CH2:9]([O:11][C:12](=[O:38])[CH:13]([C:14]1[CH:15]=[C:16]([C:28]2[CH:29]=[CH:30][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:33]=2)[CH:17]=[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=1)[CH2:2][CH2:3][CH3:4])[CH3:10]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 336431-IodopropaneHCID 2724682Lithium diisopropylamideHCID 24771790Ethyl [5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]acetate

Product 1

HCID 24771799Ethyl 2-[5-benzyloxy-4'-(trifluoromethyl)biphenyl-3-yl]pentanoateYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LDA (4.5 mL of 1.8 M in THF, 8 mmol) was added dropwise to a stirred solution of (5-Benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (3 g, 7.3 mmol) in THF (50 mL) at −78° C. The reaction mixture was stirred for 30 minutes at −78° C. before iodopropane (0.85 mL, 8.7 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight. A saturated aqueous solution of ammonium chloride (10 mL) was carefully added and the residue was partitioned between EtOAc and water. The aqueous layers were extracted with EtOAc (×3). The combined organic layers were washed with water, brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (EtOAc:petroleum ether) to give 2-(5-Benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (2.2 g) as an oil in 66% yield.

Workup

  1. additionwas added dropwise
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layers were extracted with EtOAc (×3)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography (EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-2fdf3d229ced4114b5fb090cd333d2c4
Source dataset
uspto-grants-2009_07
Patent number
US07557244B2

Reaction notes

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