Water → 5-Chloro-alpha-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol

HRID 1772

반응식

HRID 1772 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:21]=1[CH:22]=O.[BH4-].[Na+].O>C(O)(=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:2]([NH:1][CH2:22][C:21]2[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:20]=2[O:19][CH3:18])=[C:3]([CH:13]=1)[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11]

참가 물질

6

반응물 4

HCID 962WaterHCID 691752,4-DimethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 11437092(2-Amino-5-chlorophenyl)(2-chlorophenyl)methanol

생성물 1

HCID 538414955-Chloro-alpha-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol수율 96.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of 2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol (5.0 g) and 2,4-dimethoxy benzaldehyde (3.72 g) in acetic acid (50 ml) was added, under ice-cooling, sodium borohydride (0.94 g). The mixture was stirred for one hour at room temperature, which was poured into water (200 ml), followed by extraction with ethyl acetate (200 ml×2). The ethyl acetate layer was washed with 1N sodium hydroxide, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1) to give 5-chloro-α-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol (7.5 g) as an oily product.

후처리

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate (200 ml×2)
  3. washThe ethyl acetate layer was washed with 1N sodium hydroxide, which
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-8208d819f879448fbecf7d2aa5f1ad04
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726306

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