Sodium borohydride → 3-Hydroxycyclobutyl 2,2-dimethylpropanoate

HRID 552808Notes

Reaction equation

HRID 552808 reaction equation
[C:1]([O:7][CH:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[BH4-].[Na+]>C(O)C>[C:1]([O:7][CH:8]1[CH2:9][CH:10]([OH:12])[CH2:11]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 533969923-Oxocyclobutyl pivalate

Product 1

HCID 575158713-Hydroxycyclobutyl 2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-oxocyclobutyl pivalate (15.1 g, 88.7 mmol) in ethanol (100 ml) at 0° C. was added sodium borohydride (4.69 ml, 133 mmol) in several portions. The reaction was stirred for 30 min, slowly quenched with 10% aqueous HCl and concentrated to remove ethanol. The solution was taken up with more 10% HCl, extracted with DCM (3×), washed with brine, dried over MgSO4 and concentrated to give the title compound as a light yellow oil.

Workup

  1. customslowly quenched with 10% aqueous HCl
  2. concentrationconcentrated
  3. customto remove ethanol
  4. extractionextracted with DCM (3×)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-eb16f1145739487d9699aaef36c1fd10
Source dataset
uspto-grants-2011_05
Patent number
US07951838B2

Reaction notes

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