Hydrochloric Acid → {4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-methanol

HRID 405702Notes

Reaction equation

HRID 405702 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([CH3:28])[O:13][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[CH:15]=2)=[CH:7][C:6]=1[CH3:29])C.[BH4-].[Na+].CO.Cl>O1CCCC1.C(OCC)C>[Cl:27][C:22]1[CH:21]=[C:20]([C:14]2([C:16]([F:18])([F:17])[F:19])[O:13][N:12]([CH3:28])[C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][OH:3])=[C:6]([CH3:29])[CH:7]=3)=[CH:15]2)[CH:25]=[C:24]([Cl:26])[CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 533715074-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid ethyl ester

Product 1

HCID 53371509{4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-methanolYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

414 mg of 4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid ethyl ester (VIIIa) and 152 mg of sodium borohydride were suspended in 10 ml tetrahydrofurane. The mixture was heated to 60° C. and 0.85 ml of methanol was the added dropwise under vigorous stirring. The mixture was stirred at 60° C. until the gas evolution subsided. The mixture was then cooled and ice water followed by diethylether were added. Then a solution of hydrochloric acid (1N) was slowly added to acidify the solution. The organic phase was washed with water and dried. Evaporation of the solvent afforded {4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-phenyl}-methanol as a solidified foam in 98% yield. 1H-NMR (CDCl3, δ in ppm): 7.28-7.45 (m, 6H), 5.34 (s, 1H), 4.72 (s, 2H), 2.99 (s, 3H), 2.35 (s, 3H).

Workup

  1. additionadded dropwise under vigorous stirring
  2. temperatureThe mixture was then cooled
  3. additionwere added
  4. washThe organic phase was washed with water
  5. customdried
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0a35f25392fb4099a779cbbaac661533
Source dataset
uspto-grants-2014_06
Patent number
US08754053B2

Reaction notes

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