Methyl 3,5-dioxohexanoate → Methyl 3-hydroxy-5-oxohexanoate

HRID 628817Notes

Reaction equation

HRID 628817 reaction equation
[O:1]=[C:2]([CH2:8][C:9](=[O:11])[CH3:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5]>C1COCC1.[Ru](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:1][CH:2]([CH2:8][C:9](=[O:11])[CH3:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 538296Methyl 3,5-dioxohexanoate

Product 1

HCID 14689085Methyl 3-hydroxy-5-oxohexanoateYield 52%

Reagents, catalysts & solvents 2

HCID 11007548Dichlorotris(triphenylphosphine)rutheniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3,5-dioxohexanoate (19.0 g) was dissolved in THF (380 mL) and tris(triphenylphosphine) ruthenium (II) dichloride (1.1 g) was added. The reaction mixture was hydrogenated at 5 bar, 50° C. for 16 h and then cooled to room temperature. The solvent was removed under vacuum and the oil was purified on silica gel (hexane/EtOAC 1:1) to give the final methyl 3-hydroxy-5-oxohexanoate (10 g).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe oil was purified on silica gel (hexane/EtOAC 1:1)

Sources & evidence

ORD record
ord-0bec360ef86845a78b867354a2526b68
Source dataset
uspto-grants-2016_04
Patent number
US09315470B2

Reaction notes

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