Diethyl Ether → 1,1-Dimethylethyl tetrahydro-4-hydroxy-3-furancarboxylate

HRID 1361294Notes

Reaction equation

HRID 1361294 reaction equation
C(C1C(C(O)=O)C(=O)CO1)(C)(C)C.[O:14]=[C:15]1[CH2:19][O:18][CH2:17][CH:16]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[BH4-].[Na+].CCOCC>C(O)(C)C>[OH:14][CH:15]1[CH2:19][O:18][CH2:17][CH:16]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4311764Sodium borohydride2×HCID 112292044-Oxo-Tetrahydro-Furan-3-Carboxylic Acid Tert-Butyl EsterHCID 66970985HCID 66970985, compound

Product 1

HCID 114128161,1-Dimethylethyl tetrahydro-4-hydroxy-3-furancarboxylateYield 86.56%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The product of Step A, tert-butyl 4-oxotetrahydrofuran-3-carboxylate (0.95 g, 5.10 mmol) was placed in isopropylalcohol (14 mL) at 0-5° C., NaBH4 (77 mg, 2.04 mmol) was added, and stirred for 2 h. NaBH (77 mg, 2.04 mmol) was added again, and stirred at rt for 1 h, NaBH4 (39 mg, 1.02 mmol) was added, and stirred for 30 min. The reaction mixture was treated with Et2O to dilute, washed with brine, and extracted with Et2O twice. The organic layer was collected, extracted with a NaHCO3 aqueous solution, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/3) to give the title compound (0.83 g, 86.56%).

Workup

  1. stirringstirred at rt for 1 h
  2. stirringstirred for 30 min
  3. additionto dilute
  4. washwashed with brine
  5. extractionextracted with Et2O twice
  6. customThe organic layer was collected
  7. extractionextracted with a NaHCO3 aqueous solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/3)

Sources & evidence

ORD record
ord-acd147be3cf84ec98cf0254f6fb0e604
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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