Water → HCID 22600079, compound

HRID 1760032Notes

Reaction equation

HRID 1760032 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH:21]=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][C:10]=1[O:23][CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH2:21][OH:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][C:10]=1[O:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22600123HCID 22600123, compound

Product 1

HCID 22600079HCID 22600079, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of ethyl 2-(4-benzyloxy-3-methoxyphenyl)-3-oxo-propionate (1.356 g; 3.47 mmol; from step (ii) above) in MeOH:CH2Cl2 (3:1, 20 mL) was cooled to −15 to −5° C., and NaBH4 (0.264 g; 6.95 mmol) was added in portions. The cooled reaction mixture was stirred, whereafter it was allowed to attain room temperature. Water was added, and the mixture was partially concentrated. After extraction with EtOAc (2×25 mL), washing of the organic phase with brine, drying (Na2SO4) and evaporation, 1.32 g (97.1%) of the sub-title compound was obtained.

Workup

  1. customThe cooled reaction mixture
  2. customto attain room temperature
  3. concentrationthe mixture was partially concentrated
  4. extractionAfter extraction with EtOAc (2×25 mL)
  5. washwashing of the organic phase with brine
  6. customdrying
  7. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-2f5b325bc1044042b245a12e0d38a809
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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