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

HRID 854938노트

반응식

HRID 854938 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([S:12][CH3:13])[CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2.[OH-].[Na+]>C1COCC1.CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([S:12][CH3:13])[CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 69517271ethyl 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

생성물 1

HCID 589345476-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid수율 71%

시약·촉매·용매 1

HCID 18504229Ethanol tetrahydrofuran water용매

실험 절차

To a stirred solution of ethyl 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylate (Step 3, 0.203 g, 0.575 mmol) in THF:EtOH:H2O (7:2:1, 5 mL), was added aqueous sodium hydroxide (0.63 mmol, 0.25 mL of 2.5 N soln.) and allowed to stir for two days. The resulting clear, yellow solution was concentrated in vacuo, was diluted with water (35 mL), and was acidified with concentrated HCl resulting in formation of a yellow suspension. Vacuum filtration of the suspension yielded the title compound as a yellow powder (0.132 g, 71%). 1HNMR (acetone-d6/300 MHz) 7.87 (s, 1H), 7.34 (d, J=2.2 Hz, 1H), 7.25 (d, J=2.2 Hz, 1H), 5.93 (q, 1H, J=7.05 Hz), 2.53 (s, 3H). LRMS m/z 323 (M−H); ESHRMS m/z 322.9782 (M−H, C12H7F3O3ClS, Calc'd 322.9757). Anal. Calc'd for C12H8F3O3ClS: C, 44.39; H, 2.48. Found: C, 44.63; H, 2.52.)

후처리

  1. concentrationThe resulting clear, yellow solution was concentrated in vacuo
  2. additionwas diluted with water (35 mL)
  3. filtrationVacuum filtration of the suspension

출처 및 근거

ORD 기록
ord-e28846c605c94fb6b05624c8b10243aa
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

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