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

HRID 854859ノート

反応式

HRID 854859 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21864137Acetonitrile methanol water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3770f3cbda164067a85a93dcf4b83e9e
出典データセット
uspto-grants-2007_08
特許番号
US07259266B2

反応ノート

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