6-[((2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate → 6-[((2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)-phenyl]-methoxy}-phenyl)-prop-2-enoyl)oxy]hexyl 3,5-diaminobenzoate

HRID 511711ノート

反応式

HRID 511711 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:45]=[C:46]([N+:48]([O-])=O)[CH:47]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:44])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:43])([F:42])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][C:38]([F:41])([F:40])[F:39])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)=[O:8])([O-])=O>CN(C)C=O.O.[Zn]>[NH2:48][C:46]1[CH:45]=[C:6]([CH:5]=[C:4]([NH2:1])[CH:47]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:44])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:42])([F:43])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][C:38]([F:39])([F:40])[F:41])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)=[O:8]

参加物

5

反応物 1

HCID 866765476-[((2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate

生成物 1

HCID 866765486-[((2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)-phenyl]-methoxy}-phenyl)-prop-2-enoyl)oxy]hexyl 3,5-diaminobenzoate収率 83.1%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

5.95 g (8.38 mmol) of 6-[((2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)phenyl]methoxy}phenyl)-prop-2-enoyl)oxy]-hexyl 3,5-dinitrobenzoate are dissolved in a mixture of 54 mL of N,N-di-methylformamide and 6 mL water. 13.9 g (51.4 mmol) ferric chloride hexahydrate is added. 5.60 g (85.7 mmol) zinc powder is added portion wise within 60 minutes. The mixture is allowed to react for 2 hours. The reaction mixture is partitioned between ethyl acetate and water and filtrated. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtrated and concentrated under reduced pressure. Filtration of the residue on 200 g silica gel using toluene:ethyl acetate 1:3 as eluent and crystallization from ethyl acetate:hexane mixture yields 4.53 g of 6-[((2E)-3-(4-{difluoro[4-(4,4,4-trifluorobutoxy)-phenyl]-methoxy}-phenyl)-prop-2-enoyl)oxy]hexyl 3,5-diaminobenzoate as yellow crystals.

後処理

  1. customto react for 2 hours
  2. customThe reaction mixture is partitioned between ethyl acetate and water
  3. filtrationfiltrated
  4. washThe organic phase is washed repeatedly with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. filtrationFiltration of the residue on 200 g silica gel
  9. customcrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-376d7ca2fef6429aa5834797aa012eda
出典データセット
uspto-grants-2015_08
特許番号
US09097938B2

反応ノート

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