Sodium borohydride → Ethyl 3-[3-(1-hydroxyhexyl)-4-methoxyphenyl)propanoate

HRID 1455692Notes

Reaction equation

HRID 1455692 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:10]=1)[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:10]=1)[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69051926Ethyl 3-(3-hexanoyl-4-methoxyphenyl)propanoate

Product 1

HCID 69619229Ethyl 3-[3-(1-hydroxyhexyl)-4-methoxyphenyl)propanoateYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

NaBH4 (7.6 g; 0.2 mol) is added in small amounts to 61 g (0.2 mol) of ethyl3-(3-hexanoyl-4-methoxyphenyl)propanoate, as a solution in 500 ml of ethanol. The mixture is heated for 1 hour at 80° C. After 16 hours at room temperature, the mixture is concentrated under vacuum and poured into saturated sodium chloride solution. The resulting mixture is extracted with ether and the organic phase is dried over sodium sulfate. Evaporation of the solvents gives 58 g of product in a 94% yield.

Workup

  1. concentrationthe mixture is concentrated under vacuum
  2. additionpoured into saturated sodium chloride solution
  3. extractionThe resulting mixture is extracted with ether
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-e655434542f747a2b693002df7d4469e
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

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