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

HRID 2423443ノート

反応式

HRID 2423443 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c7ecf939c7df43629b00fca4e4dd2e50
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

読み込み中…