Water → HCID 22600125, compound

HRID 1760017Notes

Reaction equation

HRID 1760017 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-e058df46fc6e41939d7d3ae52f1719ab
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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