Ammonium Chloride → 2-(4,4''-Dichloro-[1,1';3',1'']terphenyl-5'-yl)-pentanoic acid methyl ester

HRID 426310Notes

Reaction equation

HRID 426310 reaction equation
[Li+].[CH3:2][CH:3]([N-]C(C)C)[CH3:4].[CH3:9][O:10][C:11](=[O:33])[CH2:12][C:13]1[CH:14]=[C:15]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH:18]=1.ICCC.[Cl-].[NH4+]>C1COCC1.O.CCOC(C)=O>[CH3:9][O:10][C:11](=[O:33])[CH:12]([C:13]1[CH:14]=[C:15]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH:16]=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[CH:18]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 336431-IodopropaneHCID 2724682Lithium diisopropylamideHCID 66702504(4,4''-Dichloro-[1,1';3',1'']terphenyl-5'-yl)-acetic acid methyl ester

Product 1

HCID 667024852-(4,4''-Dichloro-[1,1';3',1'']terphenyl-5'-yl)-pentanoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of LDA (0.18 mL of 1.8 M in THF, 0.31 mmol) was added dropwise to a stirred solution of (4,4″-dichloro-[1,1′;3′,1″]terphenyl-5′-yl)-acetic acid methyl ester (100 mg, 0.26 mmol) in THF (10 mL) at −78° C. The reaction mixture was stirred for 30 minutes at −78° C. before iodopropane (0.035 mL, 0.31 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 partitionned 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) yield 70 mg (66%) 1H NMR (CDCl3) δ 7.60 (t, 1H), 7.55 (d, 4H), 7.48 (d, 2H), 7.42 (d, 4H), 3.65-3.72 (m, 4H), 2.11-2.23 (m, 1H), 1.78-1.89 (m, 1H), 1.28-1.40 (m, 4H), 0.94 (t, 3H)

Workup

  1. additionwas added dropwise
  2. extractionThe aqueous layers were extracted with EtOAc (×3)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (EtOAc:petroleum ether) yield 70 mg (66%) 1H NMR (CDCl3) δ 7.60 (t, 1H), 7.55 (d, 4H), 7.48 (d, 2H), 7.42 (d, 4H), 3.65-3.72 (m, 4H), 2.11-2.23 (m, 1H), 1.78-1.89 (m, 1H), 1.28-1.40 (m, 4H), 0.94 (t, 3H)

Sources & evidence

ORD record
ord-d6a14b785ee74eb08473689016d37785
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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