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

HRID 854938ノート

反応式

HRID 854938 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 18504229Ethanol tetrahydrofuran water溶媒

実験手順

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.)

後処理

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

出典と根拠

ORDレコード
ord-e28846c605c94fb6b05624c8b10243aa
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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