Tetrahydrofuran ethanol → (5-(2-Methyl-1,3-dioxolan-2-yl)isoxazol-3-yl)methanol

HRID 416275Notes

Reaction equation

HRID 416275 reaction equation
[CH3:1][C:2]1([C:7]2[O:11][N:10]=[C:9]([C:12](OCC)=[O:13])[CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.CCO.C1COCC1>O>[CH3:1][C:2]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1

Participants

4

Reactant 2

HCID 21873804Tetrahydrofuran ethanolHCID 58930452Ethyl 5-(2-methyl-1,3-dioxolan-2-yl)isoxazole-3-carboxylate

Product 1

HCID 58930623(5-(2-Methyl-1,3-dioxolan-2-yl)isoxazol-3-yl)methanolYield 93.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the dioxolane 318 (3.14 g, 13.8 mmol) in a 1:2 mixture of EtOH-THF (45 mL) NaBH4 (0.68 g, 18.0 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours, treated with water and the organic solvents were evaporated. The aqueous phase was extracted with EtOAc and combined organic layers were successively washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure to afford the title compound as oil (2.39 g, 93% yield) which was used for next step without further purification. 1H NMR (DMSO-d6) δ (ppm): 6.43 (s, 1H), 5.47 (t, J=5.9 Hz, 1H), 4.47 (d, J=5.9 Hz, 2H), 4.06-4.02 (m, 2H), 3.94-3.90 (m, 2H), 1.66 (s, 3H). MS (m/z): 185.18 (calc) 186.1 (MH+) (found).

Workup

  1. additionwas added
  2. customthe organic solvents were evaporated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washwere successively washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8e8a4c86d271424093661981e0142f22
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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