Hydrochloric Acid → Ethyl 4-cyano-3-(3-(hydroxymethyl)phenyl)-4-methylpentanoate

HRID 1049570Notes

Reaction equation

HRID 1049570 reaction equation
Cl.[C:2]([C:4]([CH3:24])([CH3:23])[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19]COC)[CH:13]=1)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:3]>CO.C(OCC)(=O)C.O>[C:2]([C:4]([CH3:23])([CH3:24])[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][OH:19])[CH:13]=1)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:3]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 117760181HCID 117760181, compound

Product 1

HCID 117759629Ethyl 4-cyano-3-(3-(hydroxymethyl)phenyl)-4-methylpentanoateYield 81.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Conc. hydrochloric acid (1.10 mL) was added to a solution of ethyl 4-cyano-3-(3-((methoxymethoxy)methyl)phenyl)-4-methylpentanoate (210 mg) in methanol (2 mL) at room temperature, and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, water was added at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a mixture (147 mg) of the title compound and methyl ester thereof. This compound was used for the next step without further purification.

Workup

  1. additionwas added at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b017765b99a9499fbffcaf99088f3027
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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