Sodium Hydroxide → 6-chloro-8-(4-chlorophenyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 722326ノート

反応式

HRID 722326 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17]CC)=[O:16])=[CH:7][C:6]=2[CH:20]=1.[OH-].[Na+]>C1COCC1.C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[C:5]2[O:10][CH:9]([C:11]([F:12])([F:14])[F:13])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 21883623ethyl 6-chloro-8-(4-chlorophenyl)-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate

生成物 1

HCID 218836046-chloro-8-(4-chlorophenyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid収率 86%

試薬・触媒・溶媒 1

HCID 18504229Ethanol tetrahydrofuran water溶媒

実験手順

The ester from Step 1 (0.500 g, 1.20 mmol) was dissolved in a solution of THF:ethanol:water (7:2:1; 10 mL), treated with sodium hydroxide (0.48 mL, 1.20 mmol of a 2.5 N solution), and stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was dissolved in water (10 mL). Diethyl ether (10 mL) was added and the mixture acidified with concentrated HCl. The organic layer was separated, and the aqueous phase was extracted with diethyl ether (2×10 mL). The combined extracts were dried over MgSO4, filtered, and evaporated to yield a white solid, which was recrystallized in diethyl ether-hexane to afford the title compound as a white solid (0.40 g, 86%): mp 205.5–207.3° C. 1H NMR (CDCl3/300 MHz) 7.81 (s, 1H), 7.42(s, 4H), 7.34 (d, 1H, J=2.4 Hz), 7.25 (s, 1H), 5.69 (q, 1H, J=6.8 Hz). FABLRMS m/z 387 (M−H). ESHRMS m/z 386.9788 (M−H, Calc'd. 386.980259). Anal. Calc'd. for C17H9Cl2F3O3: C, 52.47; H, 2.33; Cl, 18.22. Found: C, 52.38; H, 2.47; Cl, 18.20.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. additionDiethyl ether (10 mL) was added
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with diethyl ether (2×10 mL)
  6. dry with materialThe combined extracts were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto yield a white solid, which
  10. customwas recrystallized in diethyl ether-hexane

出典と根拠

ORDレコード
ord-9d2ecb9e133a4d7086f3c2d4ac1d59a3
出典データセット
uspto-grants-2006_11
特許番号
US07138411B2

反応ノート

読み込み中…