Water → HCID 59675048, compound

HRID 1010695Notes

Reaction equation

HRID 1010695 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])=[C:12]([C:22]([CH3:25])([CH3:24])[CH3:23])[O:11][N:10]=1.[BH4-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([CH:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[OH:15])=[C:12]([C:22]([CH3:25])([CH3:24])[CH3:23])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67313917HCID 67313917, compound

Product 1

HCID 59675048HCID 59675048, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 92 mg (0.24 mmol) of 3-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-4-[(3-pyridyl)carbonyl]isoxazole in 5 mL of ethanol at 0° C. was added 20 mg (0.53 mmol) of sodium borohydride. After 2 hr, the reaction mixture was poured into water, and the product was extracted several times with ethyl acetate. The combined ethyl acetate fractions were washed with saturated sodium chloride and dried over magnesium sulfate. The drying agent was filtered off, and the ethyl acetate was removed by rotoevaporation. The crude product was purified by prep TLC to yield 68 mg (0.18 mmol) 3-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-4-[(3-pyridyl)hydroxy-methyl]isoxazole. 1H NMR (CDCl3): δ 1.52 (s, 9), 6.14 (br s, 1), 6.86 (d, 1), 7.38 (m, 1), 8.27 (br s, 1) and 8.33 ppm (m, 1). MS m/z: 377.0 (M+H).

Workup

  1. extractionthe product was extracted several times with ethyl acetate
  2. washThe combined ethyl acetate fractions were washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe ethyl acetate was removed by rotoevaporation
  6. customThe crude product was purified by prep TLC

Sources & evidence

ORD record
ord-0008c1f6249d4ea298a3fdf7f284c444
Source dataset
uspto-grants-2011_07
Patent number
US07977341B2

Reaction notes

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