Ethyl Acetate → Tert-butyl 3-hydroxy-2,2-dimethylpropanoate

HRID 661466Notes

Reaction equation

HRID 661466 reaction equation
C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].O1CCCC1.[CH3:23][C:24]([CH3:36])([C:32](OC)=[O:33])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[C:28]([O:27][C:25](=[O:26])[C:24]([CH3:36])([CH3:23])[CH2:32][OH:33])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 155777421-Tert-butyl 3-methyl 2,2-dimethylmalonateHCID 131723922lithium tri-t-butoxyaluminohydride THF

Product 1

HCID 54272639Tert-butyl 3-hydroxy-2,2-dimethylpropanoateYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1M lithium tri-tert-butoxy-aluminohydride/tetrahydrofuran solution (14 ml) was added dropwise to a solution of tert-butyl methyl 2,2-dimethyl-malonate (1.12 g) in tetrahydrofuran (30 ml) under nitrogen atmosphere over 15 minutes and the mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature, a saturated ammonium chloride aq. solution and ethyl acetate were added and the organic layer was separated, washed with water and a saturated brine, dried over magnesium sulfate and concentrated in vacuo to give the titled compound (800 mg). MS (m/z): 175 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated brine, dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8990923d73b84037b6ceeb47438a817e
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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