Ethanol → HCID 21834382, compound

HRID 1741001Notes

Reaction equation

HRID 1741001 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([O:16]CC)=O)=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[BH4-].[Na+].[CH2:21](O)[CH3:22]>O>[CH2:21]([CH:14]([OH:16])[CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:11][CH:10]=1)[CH3:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 11207441ethyl 3-(4-carboethoxyphenyl)propionate

Product 1

HCID 21834382HCID 21834382, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The ethyl 3-(4-carboethoxyphenyl)propionate (1.23 g, 4.91 mmol) was dissolved in 11 ml of absolute ethanol, cooled in an ice bath, and treated with 0.25 ml of a 2 N cupric sulfate solution in water. Sodium borohydride (0.93 g, 24.6 mmol) was added in small portions over one hour. The reaction was stirred at room temperature over night and then evaporated. The residue was slurried in brine and extracted twice with chloroform. The extracts were filtered through celite, dried over MgSO4, and concentrated to afford 1.0 g (98%) of the subtitle compound.

Workup

  1. temperaturecooled in an ice bath
  2. customevaporated
  3. extractionextracted twice with chloroform
  4. filtrationThe extracts were filtered through celite
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7600939b05644574a72400fa7d9f2d0f
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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