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

HRID 2423443노트

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HRID 2423443 반응식
[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

참가 물질

5

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-c7ecf939c7df43629b00fca4e4dd2e50
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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