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Sodium Hydroxide → HCID 21883490, 화합물

HRID 722328
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HRID 722328 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[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:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)[C:5]2[O:10][CH:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:20]=1
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 21883708HCID 21883708, 화합물

생성물 1

HCID 21883490HCID 21883490, 화합물수율 82.2%

시약·촉매·용매 1

HCID 18504229Ethanol tetrahydrofuran water용매

실험 절차

The ester from Step 1 (0.300 g, 0.727 mmol) was dissolved in THF-ethanol-water (7:2:1, 10 mL). It was treated with sodium hydroxide (0.29 mL of a 2.5 N solution, 0.727 mmol), and stirred at room temperature for 18 hours. The solvent was evaporated and the residue was dissolved in water (10 mL). Ether (10 mL) was added, followed by a few drops of concentrated HCl. The ether layer was separated, and the aqueous phase was extracted with ether (2×10 mL). The ether extracts were combined, dried over MgSO4, filtered, and concentrated in vacuo to yield a white solid, which was recrystallized in diethyl ether-hexane to afford the title compound as a white solid (0.23 g, 81%): mp 173.1–177.4° C. 1H NMR (CDCl3/300 MHz) 7.81 (s, 1H), 7.39–7.37 (m, 2H ), 7.05–7.04 (m, 2H), 6.97–6.94 (m, 1H), 5.71 (q, 1H, J=6.7 Hz), 3.85 (s, 3H). ESHRMS m/z 383.0278 (M−H, Calc'd. 383.029796). Anal. Calc'd. for C18H12ClF3O4: C, 56.20; H, 3.14; Cl, 9.21. Found: C, 55.90; H, 3.11; Cl, 9.48.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. additionEther (10 mL) was added
  4. customThe ether layer was separated
  5. extractionthe aqueous phase was extracted with ether (2×10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield a white solid, which
  10. customwas recrystallized in diethyl ether-hexane

출처 및 근거

ORD 기록
ord-ac16f33ec05e4ea284779c0f3e938ead
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07138411B2

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