Bicarbonate Ion → 5-Phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde

HRID 1506304ノート

反応式

HRID 1506304 の反応式
[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[C:8]=2[C:14]([F:17])([F:16])[F:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-]>ClCCl>[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH:12]=[O:13])[C:8]=2[C:14]([F:16])([F:17])[F:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 769Bicarbonate IonHCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane2 回HCID 67168678HCID 67168678、化合物

生成物 1

HCID 866698695-Phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde収率 105.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a mixture of (5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)methanol (step A, 1.79 g, 7.36 mmol) in dichloromethane (23 mL) at 0° C. was added Dess-Martin Periodinane (3.43 g, 8.10 mmol). The reaction mixture was stirred at 0° C. for 10 min. and then at room temperature for 30 min. An additional 1.0 g of the Dess-Martin Periodinane was added, and the reaction mixture was stirred for an additional 30 min. A 1:1 mixture of saturated aqueous sodium thiosulfate and saturated aqueous bicarbonate (50 mL) was added slowly. The organic layer was collected, and the aqueous layer was extracted with dichloromethane (50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduce pressure to give 5-phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde (1.87 g, 7.75 mmol, quantitative yield) as a pale yellow oil. The compound had an HPLC ret. time=2.09 min. (condition A).

後処理

  1. waitat room temperature for 30 min
  2. stirringthe reaction mixture was stirred for an additional 30 min
  3. additionwas added slowly
  4. customThe organic layer was collected
  5. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-282bc2384a444b0c84a0f7abfc23669a
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…