Water → HCID 22600125, compound

HRID 1383358Notes

Reaction equation

HRID 1383358 reaction equation
[O:1]=[CH:2][CH:3]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([O:16][CH3:17])[CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[BH4-].[Na+].O>CO>[OH:1][CH2:2][CH:3]([C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([O:16][CH3:17])[CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22600129HCID 22600129, compound

Product 1

HCID 22600125HCID 22600125, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

Procedure

A stirred solution of ethyl 3-oxo-2-(3-methoxy-5-methylphenyl)propionate (1.9 g; 8.1 mmol; from step (v) above) in MeOH (50 mL) was cooled to −15° C. NaBH4 (0.61 g; 16 mmol) was then added in portions. The mixture was stirred for 3 hours at −15 to −5° C. Water was then added, and resultant mixture concentrated. The aqueous phase was extracted with EtOAc, the organic phase was washed with water, dried (Na2SO4) and evaporated to yield 2.0 g (59%) of sub-title compound.

Workup

  1. concentrationresultant mixture concentrated
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-651d9b2649b547ff8aececfd8f2b8616
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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