Sodium borohydride → HCID 59759989、化合物

HRID 1672418ノート

反応式

HRID 1672418 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[C:9]=1[C:21]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)=[O:22].[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[C:9]=1[CH:21]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[OH:22]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 67313482HCID 67313482、化合物

生成物 1

HCID 59759989HCID 59759989、化合物収率 78.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 80 mg (0.19 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)carbonyl]isoxazole in 3 mL of ethanol at 0° C. was added 40 mg (1.06 mmol) of sodium borohydride. The mixture was stirred for 2 hrs and then diluted with ethyl acetate. The ethyl acetate solution was washed with saturated sodium chloride solution and dried over magnesium sulfate. The drying agent was filtered off, and the ethyl acetate was removed by rotoevaporation. The crude product was purified by prep TLC to give 65 mg (0.15 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]-isoxazole. 1H NMR (CDCl3): δ 5.80 (br s, 1), 6.97 (m,1), 8.23 (br s, 1), and 8.28 ppm (br s, 1). MS m/z: 431.0 (M+H).

後処理

  1. washThe ethyl acetate solution was washed with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. customthe ethyl acetate was removed by rotoevaporation
  5. customThe crude product was purified by prep TLC

出典と根拠

ORDレコード
ord-606757f6196240da91cfed66afc2c309
出典データセット
uspto-grants-2011_08
特許番号
US07998983B2

反応ノート

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