Dimethyl 3-oxoglutarate → Dimethyl 3-hydroxypentanedioate

HRID 472970Notes

Reaction equation

HRID 472970 reaction equation
[O:1]=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[BH4-].[Na+]>CO>[OH:1][CH:2]([CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 74591Dimethyl 3-oxoglutarateHCID 4311764Sodium borohydride

Product 1

HCID 232491Dimethyl 3-hydroxypentanedioateYield 44.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of dimethyl 3-oxopentanedioate (20 g, 115 mmol) in anhydrous MeOH (140 mL) was added NaBH4 (2.33 g, 63.18 mmol) in small portions over 10 minutes. The mixture was stirred for 1 h at room temperature and concentrated. Water and EtOAc was added and the organic phase was separated and dried. The combined organic layer was concentrated to give the crude product, which was purified by column chromatography to give dimethyl 3-hydroxypentanedioate (9 g, 44%). 1H-NMR (CDCl3): 2.51 (m, 4H), 3.43 (m, 1H), 3.70 (m, 6H), 4.45 (m, 1H).

Workup

  1. concentrationconcentrated
  2. additionWater and EtOAc was added
  3. customthe organic phase was separated
  4. customdried
  5. concentrationThe combined organic layer was concentrated
  6. customto give the crude product, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f11c2c15a4774fc6b18a47ed141f17a6
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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