Hydrochloric Acid → Diethyl 3-hydroxy-2-(2-methylpropyl)pentanedioate

HRID 1031246

Reaction equation

HRID 1031246 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]([CH3:20])[CH2:5][CH:6]([C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl>C(O)C.O>[OH:19][CH:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]([CH2:5][CH:4]([CH3:3])[CH3:20])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 99926592-Isobutyl-3-ketoglutarate diethyl ester

Product 1

HCID 10377906Diethyl 3-hydroxy-2-(2-methylpropyl)pentanedioateYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (1.1 g, 29 mmol) was added to an ice-cold solution of diethyl 2-(2-methylpropyl)-3-oxopentanedioate (7.5 g, 29 mmol) in ethanol (75 ml). The mixture was stirred at 5°-10° C. for 2 h, then 2 N hydrochloric acid (18 ml) was added slowly at 0° C., and the mixture was stirred at room temperature for 45 min. The mixture was diluted with water (400 ml), then was extracted with ethyl acetate (4×100 ml). The extracts were washed with water (2×100 ml) and brine (100 ml), then were dried (Na2SO4) and evaporated in vacuo to leave the title compound as an oil (7.5 g, 100%).

Workup

  1. stirringthe mixture was stirred at room temperature for 45 min
  2. extractionwas extracted with ethyl acetate (4×100 ml)
  3. washThe extracts were washed with water (2×100 ml) and brine (100 ml)
  4. dry with materialwere dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-f48c096ec1fb49babed39629cdb25f75
Source dataset
uspto-grants-1992_04
Patent number
US05109000

Linked notes

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