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

HRID 2214885

반응식

HRID 2214885 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 18504229Ethanol tetrahydrofuran water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fd9d50ca624549fc85a160f9a0a1bef4
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109211B2

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