Methyl morpholine oxide → 3-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

HRID 1506497ノート

反応式

HRID 1506497 の反応式
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH:25]=C)=[CH:19][CH:18]=5)[C:8]=2[C:27]([F:30])([F:29])[F:28])[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[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH:25]=[O:35])=[CH:19][CH:18]=5)[C:8]=2[C:27]([F:28])([F:30])[F:29])[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 671704243-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

生成物 1

HCID 866698753-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde収率 100%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a clear solution of 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 6A, 1.6 g, 3.92 mmol) in THF (15 mL) were sequentially added NMO (50% in water, 1.219 mL, 5.88 mmol) and osmium tetroxide (4% in water, 0.958 mL, 0.157 mmol) at room temperature. The solution was vigorously stirred at room temperature overnight. A cloudy solution of sodium periodate (1.425 g, 6.66 mmol) in water (14 mL) was added. The mixture was stirred at room temperature under nitrogen for 0.5 hr. Water (20 mL) was then added and the mixture was stirred at room temperature for 30 min. The solid was filtered, washed with water (2×2 mL) and methanol (2 mL) and dried to give 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (1.6 g, 3.90 mmol, 100% yield) as a white solid. The compound had an HPLC retention time=4.02 min. (condition C); LC/MS M+1=410.9.

後処理

  1. customat room temperature
  2. stirringThe mixture was stirred at room temperature under nitrogen for 0.5 hr
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. filtrationThe solid was filtered
  5. washwashed with water (2×2 mL) and methanol (2 mL)
  6. customdried

出典と根拠

ORDレコード
ord-a2597f999a714c11aaa9e0e5cc677d8d
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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