Triethylamine → (3-Isobutoxy-5-methyl-isoxazol-4-yl)-methanol

HRID 1807536Notes

Reaction equation

HRID 1807536 reaction equation
[CH2:1]([O:5][C:6]1[C:10]([C:11](O)=[O:12])=[C:9]([CH3:14])[O:8][N:7]=1)[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O>[CH2:1]([O:5][C:6]1[C:10]([CH2:11][OH:12])=[C:9]([CH3:14])[O:8][N:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 666436993-Isobutoxy-5-methyl-isoxazole-4-carboxylic acid

Product 1

HCID 66643582(3-Isobutoxy-5-methyl-isoxazol-4-yl)-methanolYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-isobutoxy-5-methyl-isoxazole-4-carboxylic acid (146 mg, 0.73 mmol) and triethylamine (74 mg, 0.73 mmol) in tetrahydrofuran (5 mL) at −10° C. and under argon was added ethyl chloroformate (80 mg, 1.46 mmol). After 30 min, the mixture was filtered and the filter cake washed with tetrahydrofuran (4 mL). The combined filtrates were added to a solution of sodium borohydride (69 mg, 1.83 mmol) in water (2 mL) at 5° C. After 2 h the mixture was concentrated in vacuo, diluted with NaOH (2 N, 4 mL) then dried, filtered and concentrated in vacuo to give the title compound (111 mg, 82%) as a pale yellow oil. MS: m/e=186.3 [M+H]+.

Workup

  1. filtrationthe mixture was filtered
  2. washthe filter cake washed with tetrahydrofuran (4 mL)
  3. concentrationAfter 2 h the mixture was concentrated in vacuo
  4. additiondiluted with NaOH (2 N, 4 mL)
  5. customthen dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b09dd0b4508b4cb8925273028e508290
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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