Hydrochloric Acid → 6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic Acid

HRID 854859노트

반응식

HRID 854859 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Cl)[C:11]=1O)[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-].[Li+].Cl>CO.C(#N)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:15])[F:16])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69517486ethyl 6,8-dichloro-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate

생성물 1

HCID 97956526-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic Acid수율 70.5%

시약·촉매·용매 1

HCID 21864137Acetonitrile methanol water용매

실험 절차

A solution of the ester from Step 2 (0.20 g, 0.56 mmole) was dissolved in 3 mL mixture of MeOH/ACN/H2O=1/1/1, treated with lithium hydroxide (81 mg, 3.36 mmole) and stirred at room temperature for 2 days. The reaction mixture was acidified with 1.0 N HCl to pH=1 and was extracted with EtOAc. The organic layer was washed with water,dried over anhydrous MgSO4, and filtered. The filtrate was evaporated and dried in vacuo to afford the title compound as a yellow solid (0.11 g, 60%): ESHRMS m/z 326.9438 (M−H, C11H4O4F3Cl2, Calc'd 326.9433). 1H NMR (acetone-d6/400 MHz) 7.82 (s, 1H), 7.46(s, 1H), 6.00 (q, 1H, J=7.0 Hz).

후처리

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with water,dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-3770f3cbda164067a85a93dcf4b83e9e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

반응 노트

불러오는 중…