Dichloromethane → 3-Phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanimidate

HRID 126976

反応式

HRID 126976 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.[O:15]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ClCCl>CCOCC.F[B-](F)(F)F.[Ag+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9](=[NH:11])[O:10][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:23]=2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 128981762-(4-Chlorophenyl)-3-methylbutanamide

生成物 1

HCID 128981773-Phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanimidate

試薬・触媒・溶媒 2

HCID 159722Silver tetrafluoroborate触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a refluxing solution of 2.72 g (12.9 mmol) of 2-(4-chlorophenyl)-3-methylbutyramide and 2.27 g (8.6 mmol) of 3-phenoxybenzyl bromide in a solution of 15 ml dichloromethane and 3 ml ethyl ether is added a solution of 1.83 g (9.5 mmol) of silver tetrafluoroborate in ether. The mixture is refluxed for 2 hours and then separated by pouring into ice cold aqueous ethyl acetate/sodium bicarbonate. The organic phase is washed with water, dried and stripped of solvent. The residue is triturated with ether and filtered. The filtrate is concentrated and chromatographed on silica gel, eluting with 25% ethyl acetate/hexane, and then on plates using 35% ethyl acetate/hexane, to yield 3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanimidate, MS m/e 393 (M+).

後処理

  1. temperatureThe mixture is refluxed for 2 hours
  2. customseparated
  3. additionby pouring into ice cold aqueous ethyl acetate/sodium bicarbonate
  4. washThe organic phase is washed with water
  5. customdried
  6. customThe residue is triturated with ether
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated
  9. customchromatographed on silica gel
  10. washeluting with 25% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-2e3a9f3858cd4cdd9377665e6ee2c8c1
出典データセット
uspto-grants-1981_03
特許番号
US04254264

関連ノート

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