Methanol → Benzo[d]isoxazol-3-ylmethanol

HRID 472142Notes

Reaction equation

HRID 472142 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10](OCC)=[O:11])=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][OH:11])=[N:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14177940Ethyl 1,2-benzoxazole-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 53487461Benzo[d]isoxazol-3-ylmethanolYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

589 mg (3.0 mmol) of ethyl 1,2-benzoisoxazole-3-carboxylate in solution in 10 ml of tetrahydrofuran are added to a suspension of 129 mg (3.5 mmol) of lithium aluminum hydride in 5 ml of tetrahydrofuran. The reaction mixture is stirred for one hour at 60° C. and then treated by adding 2 ml of methanol dropwise, filtered through celite and rinsed with ethyl acetate. The organic phases are combined, dried over sodium sulfate and evaporated. The residue obtained is purified by chromatography on silica gel, elution being carried out with a 60/40 heptane/ethyl acetate mixture. 180 mg (39%) of benzoisoxazol-3-ylmethanol are obtained in the form of a white solid.

Workup

  1. additiontreated
  2. filtrationfiltered through celite
  3. washrinsed with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-51104b4745534f708dc609627dc89039
Source dataset
uspto-grants-2014_01
Patent number
US08633196B2

Reaction notes

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