Ammonium Chloride → HCID 67486428, compound

HRID 2371250Notes

Reaction equation

HRID 2371250 reaction equation
[Li+].CC([N-]C(C)C)C.[CH3:9][O:10][C:11](=[O:23])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1.[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38]Br)=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+]>C1COCC1>[CH3:9][O:10][C:11](=[O:23])[CH:12]([C:13]1[CH:14]=[CH:15][C:16]([C:19]([CH3:20])([CH3:22])[CH3:21])=[CH:17][CH:18]=1)[CH2:38][C:35]1[CH:36]=[CH:37][C:32]([O:31][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 605629Methyl p-tert-butylphenylacetateHCID 2724682Lithium diisopropylamideHCID 104927561-(Benzyloxy)-4-(bromomethyl)benzene

Product 1

HCID 67486428HCID 67486428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a 2M solution of LDA in THF (5.4 mL, 10.8 mmol) in 300 mL THF cooled to −78° C. was slowly added 4-tertbutylphenyl acetic acid methyl ester (2 g, 9.8 mmol). After stirring for 1 hr at −78° C. a solution of 2.7 g of 1-benzyloxy-4-bromomethylbenzene (Chow and Mak, J. Org. Chem 1997, 62(15), 5116) in THF (10 mL) was added. The mixture was allowed to warm to room temperature overnight. Saturated ammonium chloride was added and the solution extracted with ethyl acetate. The solution was washed with brine, dried over sodium sulfate and concentrated to afford 3-(4-Benzyloxyphenyl)-2-(4-tert-butylphenyl)-propionic acid methyl ester as a yellow oil. TLC: Rf=0.42 hexane/ethyl acetate (8:1). The crude was carried on as is for the next step.

Workup

  1. additionwas added
  2. extractionthe solution extracted with ethyl acetate
  3. washThe solution was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dfc5656189da49a49f29462f5033b9e1
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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