Hydrochloric Acid → Mandestrobin 2-Demethyl

HRID 427984Notes

Reaction equation

HRID 427984 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:17])[C:13]([NH:15][CH3:16])=[O:14].[BH4-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([OH:17])[C:13]([NH:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 110877922-[2-(2,5-dimethylphenoxymethyl)phenyl]-N-methyl-2-oxoacetamide

Product 1

HCID 18357817Mandestrobin 2-DemethylYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[2-(2,5-Dimethylphenoxymethyl)phenyl]-N-methyl-2-oxoacetamide (0.93 g, 3.1 mmol) was dissolved in methanol (10 ml). Sodium borohydride (0.06 g, 1.6 mmol) was added slowly under ice-cooling. After stirring for 30 minutes, the mixture was neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate, and the solvent was evaporated to give an oil. The oil was purified by column chromatography on silica gel (eluting with n-hexane-ethyl acetate) to give the desired compound 2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-hydroxy-N-methylacetamide (0.85 g, 91%) as white crystals.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated
  6. customto give an oil
  7. customThe oil was purified by column chromatography on silica gel (eluting with n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-11a6470e7018472f98757c7c58f1cf35
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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