Ethyl Acetoacetate → ethyl (3R)-3-hydroxybutanoate

HRID 530274Notes

Reaction equation

HRID 530274 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]>CO>[OH:4][C@H:3]([CH3:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 1

HCID 8868Ethyl Acetoacetate

Product 1

HCID 440030ethyl (3R)-3-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl acetoacetate (7.5 g) and dry methanol (25 mL) were mixed and deoxygenated with flowing nitrogen for five minutes. The catalyst [(R)—Ru(BINAP)Cl2]2NEt3 (0.1 mol %) was added along with 2N HCl (0.1 mol %). The mixture was transferred to a standard Parr reactor apparatus and flushed by evacuating and refilling with hydrogen several times. The apparatus was heated at 50° C. with stirring under 100 psi of hydrogen for 16 h. After completion of reaction (monitored by TLC) the reaction was cooled and concentrated under reduced pressure. The residue was subjected to column chromatographic purification with petroleum ether/ethyl acetate (9:1 v/v) to get pure (R)-alcohol 43 as a colorless liquid.

Workup

  1. customdeoxygenated with flowing nitrogen for five minutes
  2. additionThe catalyst [(R)—Ru(BINAP)Cl2]2NEt3 (0.1 mol %) was added along with 2N HCl (0.1 mol %)
  3. customflushed
  4. customby evacuating
  5. customAfter completion of reaction (monitored by TLC) the reaction
  6. temperaturewas cooled
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was subjected to column chromatographic purification with petroleum ether/ethyl acetate (9:1 v/v)

Sources & evidence

ORD record
ord-d15ce573f601488c9b6b67f4a2a73d3e
Source dataset
uspto-grants-2016_05
Patent number
US09353077B2

Reaction notes

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