Hydrochloric Acid → tert-Butyl 2-hydroxy-4-methoxybutanoate

HRID 56768Notes

Reaction equation

HRID 56768 reaction equation
[BH4-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][C:7](=[O:15])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O.Cl>CO>[OH:15][CH:7]([CH2:6][CH2:5][O:4][CH3:3])[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 90060040Tert-butyl 4-methoxy-2-oxobutanoate

Product 1

HCID 118877948tert-Butyl 2-hydroxy-4-methoxybutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., 1.05 g (27.6 mmol) of sodium borohydride were added a little at a time to a solution of 5.20 g (27.6 mmol) of tert-butyl 4-methoxy-2-oxobutanoate in 68.5 ml of methanol. The reaction mixture was stirred for another 5 min, 5 ml of water were added and the pH was adjusted to 6 using aqueous hydrochloric acid (1N). Methanol was removed under reduced pressure at 30° C. and the aqueous phase that remained was extracted three times with 50 ml of diethyl ether. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure (25° C., 70 mbar). Yield: 4.48 g (77% of theory)

Workup

  1. customMethanol was removed under reduced pressure at 30° C.
  2. extractionthe aqueous phase that remained was extracted three times with 50 ml of diethyl ether
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure (25° C., 70 mbar)

Sources & evidence

ORD record
ord-e7189d53748641b1a81605e3b0380efe
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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