Ammonium Chloride → 3-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanol

HRID 2423443Notes

Reaction equation

HRID 2423443 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][CH2:15][CH:16]=[O:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[O:11][N:10]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][CH2:15][CH2:16][OH:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 593215603-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propanal

Product 1

HCID 593215873-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanolYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl) -4-isoxazolyl]propanal (220 mg, 0.705 mmol) in methanol (7 mL) at 0° C. was added sodium borohydride (67 mg, 1.8 mmol). The solution was stirred at 0° C. for approximately 20 minutes and was then poured into aqueous ammonium chloride. The mixture was extracted twice with ether. The combined organic layers were dried over magnesium sulfate and concentrated to afford 3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]-1-propanol (204 mg, 92%). 1H-NMR (400 MHz, CDCl3) δ 7.42-7.28 (m, 3H), 3.53 (t, J=6 Hz, 2H), 3.21 (septet, J=7 Hz, 1H), 3.35 (t, J=8 Hz, 2H), 1.57-1.50 (m, 2H), 1.38 (d, J=7 Hz, 6H).

Workup

  1. extractionThe mixture was extracted twice with ether
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c7ecf939c7df43629b00fca4e4dd2e50
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

Loading…