Trisodium Phosphate → 1236188-80-9

HRID 77112ノート

反応式

HRID 77112 の反応式
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([CH2:16][OH:17])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=[O:19].[Na+].[Na+].[Na+].Cl([O-])=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O.CC1(C)N([O])C(C)(C)CCC1>[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:13])[F:14])=[C:10]([C:16]([OH:19])=[O:17])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 4

HCID 24243Trisodium Phosphate2 回HCID 24437Sodium SulfiteHCID 23668197Sodium ChloriteHCID 66955108(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)methanol

生成物 1

HCID 583740941236188-80-9収率 99%

試薬・触媒・溶媒 3

HCID 2724126Tempo触媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
35 °C

実験手順

A mixture of (3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)methanol (2.1 g, 8.64 mmol), TEMPO (0.094 g, 0.604 mmol), and a sodium phosphate buffer (0.67M) (32.2 mL, 21.59 mmol) in acetonitrile (30 mL) was heated to 35° C. A fresh solution of sodium phosphate buffer (40 mL, pH ˜6.5) consisting of a 1:1 solution of NaH2PO4 (20 mL, 0.67M) and Na2HPO4 (20 mL, 0.67M) was prepared and used. Solutions of sodium chlorite (3.91 g, 34.5 mmol) in water (4.5 mL) and bleach (4.3 mL, 6% wt.) were added simultaneously over 40 min. The reaction was monitored by HPLC, and after 2 h, ˜30% of the starting material remained. After 6 h, 10% remained. Additional bleach (100 μL) was added, and the reaction mixture was left at room temperature overnight. Additional bleach (100 μL) was added. The resulting mixture was allowed to stir at 35° C. for additional 2 h. HPLC indicated complete conversion. The reaction was quenched by the slow addition of a solution of sodium sulfite (2.07 mL, 43.2 mmol) in water (90 mL) at 0° C., resulting in the disappearance of the brown reaction color. The solvent was removed under reduced pressure, and the remaining aqueous residue was extracted with ethyl acetate (3×40 mL). The organic layers were combined, washed with water (8 mL), washed with brine (8 mL), and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (2.2 g, 8.55 mmol, 99% yield) as a pale yellow solid.

後処理

  1. customwas prepared
  2. additionwere added simultaneously over 40 min
  3. waitAfter 6 h
  4. additionAdditional bleach (100 μL) was added
  5. waitthe reaction mixture was left at room temperature overnight
  6. additionAdditional bleach (100 μL) was added
  7. customresulting in the disappearance of the brown reaction color
  8. customThe solvent was removed under reduced pressure
  9. extractionthe remaining aqueous residue was extracted with ethyl acetate (3×40 mL)
  10. washwashed with water (8 mL)
  11. washwashed with brine (8 mL)
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-3517342d88fc4f399422327644a26e83
出典データセット
uspto-grants-2014_09
特許番号
US08835470B2

反応ノート

読み込み中…