Triethylamine → HCID 66718159, compound

HRID 1514669Notes

Reaction equation

HRID 1514669 reaction equation
[C:1]1([C:7]2[C:11]([C:12](O)=[O:13])=[C:10](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].[OH-].[Na+]>C1COCC1.O>[C:1]1([C:7]2[C:11]([CH2:12][OH:13])=[C:10](/[CH:15]=[CH:16]/[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 66718142HCID 66718142, compound

Product 1

HCID 66718159HCID 66718159, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-phenyl-5-((E)-styryl)-isoxazole-4-carboxylic acid (2.0 g, 6.9 mmol) in THF (50 mL) was added triethylamine (0.95 mL, 6.9 mmol). Then at room temperature ethyl chloroformate (0.65 mL, 6.9 mmol) was added dropwise. After 30 min the precipitated salt was filtered and washed with a small amount of THF. The filtrate was added to a solution of sodium borohydride (0.65 g, 17.1 mmol) in water (20 mL) at 5° C. After stirring for 1 h at 5° C. aqueous sodium hydroxide (2 M, 40 mL) was added. Extraction with ethyl acetate, drying over sodium sulfate, filtering and concentration afforded the title compound as a white solid (1.89 g, 99%). MS: m/e=278.1 [M+H]+.

Workup

  1. filtrationAfter 30 min the precipitated salt was filtered
  2. washwashed with a small amount of THF
  3. additionwas added
  4. extractionExtraction with ethyl acetate
  5. dry with materialdrying over sodium sulfate
  6. filtrationfiltering
  7. concentrationconcentration

Sources & evidence

ORD record
ord-e23d6066df3947ba858d765ae534ffe7
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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