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

HRID 2108275

Reaction equation

HRID 2108275 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 2N 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-cca397e3f088445fac691e9687fc6b8f
Source dataset
uspto-grants-1990_06
Patent number
US04937243

Linked notes

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