Methyl morpholine oxide → 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydro-2H-benzo[g] indazole-7-carbaldehyde

HRID 1506365ノート

反応式

HRID 1506365 の反応式
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[NH:17][N:18]=[C:19]4[C:24]=3[CH2:23][CH2:22][C:21]3[CH:25]=[C:26]([CH:29]=C)[CH:27]=[CH:28][C:20]4=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:35]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[C:1]1([C:7]2[C:11]([C:12]([F:13])([F:14])[F:15])=[C:10]([C:16]3[NH:17][N:18]=[C:19]4[C:24]=3[CH2:23][CH2:22][C:21]3[CH:25]=[C:26]([CH:29]=[O:35])[CH:27]=[CH:28][C:20]4=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 671678673-phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydro-2H-benzo[g] indazol-3-yl)isoxazole

生成物 1

HCID 866698853-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydro-2H-benzo[g] indazole-7-carbaldehyde収率 109%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 3-phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydro-2H-benzo[g]indazol-3-yl)isoxazole (Preparation 22B, 0.15 g, 0.368 mmol) in THF (2 mL) were added sequentially N-methylmorpholine N-oxide (50% aq., 0.17 mL, 0.368 mmol) and osmium tetroxide (4% aq. 0.058 mL, 7.36 μmol) at room temperature under a nitrogen atmosphere. The reaction was stirred at room temperature for 45 min. and sodium periodate (0.118 g, 0.552 mmol) in water (1 mL) was added over a period of 1 min. at room temperature. The milky heterogeneous reaction mixture was stirred at room temperature for 45 min., concentrated, and partitioned between ethyl acetate (20 mL) and water (10 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydro-2H-benzo[g]indazole-7-carbaldehyde (0.164 g, 0.401 mmol, quantitative yield) as a dark brown oil. LC/MS M+1=410.1.

後処理

  1. stirringThe milky heterogeneous reaction mixture was stirred at room temperature for 45 min.
  2. concentrationconcentrated
  3. custompartitioned between ethyl acetate (20 mL) and water (10 mL)
  4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e4d0f40dece44a8c9720197ca6c95aa3
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

読み込み中…