Boron tribromide → 5-[5-(5-Chloro-2-hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

HRID 1039214ノート

反応式

HRID 1039214 の反応式
B(Br)(Br)Br.[CH2:5]([O:7][C:8](=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[O:25]C)[O:15][N:14]=1)[CH3:6]>C(Cl)Cl>[CH2:5]([O:7][C:8](=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[OH:25])[O:15][N:14]=1)[CH3:6]

参加物

4

反応物 2

HCID 25134Boron tribromide2 回HCID 591677645-[5-(5-Chloro-2-methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

生成物 1

HCID 1364006035-[5-(5-Chloro-2-hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester収率 87.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Add boron tribromide (39 mL, 39 mmol, 1.0 M solution in CH2Cl2) dropwise to a stirred −78° C. solution of 5-[5-(5-chloro-2-methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester (4.39 g, 13 mmol) in CH2Cl2 (40 mL). Allow to warm to room temperature. After 2 hours, cool to −78° C. and add boron tribromide (13 mL, 13 mmol, 1.0 M solution in CH2Cl2) dropwise and allow to warm to room temperature overnight. Quench via dropwise addition of ethanol (60 mL, absolute). Concentrate, dissolve residue in CHCl3, wash with saturated NaHCO3 solution (×2), dry over MgSO4 and concentrate to get 3.7 g of a tan solid. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-60% EtOAc/hexanes to afford the title compound (3.3 g, 78%). MS (IS) 324 (M+1)+.

後処理

  1. temperaturecool to −78° C.
  2. temperatureto warm to room temperature overnight
  3. customQuench via dropwise addition of ethanol (60 mL, absolute)
  4. concentrationConcentrate
  5. dissolutiondissolve residue in CHCl3
  6. washwash with saturated NaHCO3 solution (×2)
  7. dry with materialdry over MgSO4
  8. concentrationconcentrate

出典と根拠

ORDレコード
ord-ad127788b56b4f67bc4762fd2d9a6a2e
出典データセット
uspto-grants-2013_10
特許番号
US08552039B2

反応ノート

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