Lithium hydroxide, monohydrate → 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 855024ノート

反応式

HRID 855024 の反応式
[I:1][C:2]1[C:3]([O:21][CH3:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]CC)=[O:17])=[CH:7]2.O.[OH-].[Li+]>O1CCCC1.O>[I:1][C:2]1[C:3]([O:21][CH3:22])=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([OH:18])=[O:17])=[CH:7]2

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 58934894ethyl 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate

生成物 1

HCID 589344428-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To the solution of 0.4 g (0.93 mmol) of ethyl 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 8 mL of tetrahydrofuran was added a solution of 155 mg (3.7 mmol) of lithium hydroxide hydrate (LiOH—H2O) in 15 mL of water. The resulting solution was heated to reflux for one h. After cooling to room temperature, the volatiles were removed, the residue was acidified at 0° C. to pH=1.5 with dilute hydrochloric acid. The product was extracted with ethyl ether. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and concd in vacuo to afford 0.30 g (81%) of a light yellow solid: 1H NMR (CDCl3/400 MHz) 7.67(s, 1H), 7.18(d, J=8.4 Hz, 1H), 6.51(d, J=8.4 Hz, 1H), 5.78(q, J=6.8 Hz, 1H), 3.92(s, 3H). MS (ESI+) 400.9 (M+1, 100). MS(ES−) 398.9(M−H, 100). HRMS (ES−) m/z calcd for (M−H; C12H7F3O4): 398.9336, found 398.9368.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for one h
  3. customthe volatiles were removed
  4. customwas acidified at 0° C. to pH=1.5 with dilute hydrochloric acid
  5. extractionThe product was extracted with ethyl ether
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate and concd in vacuo

出典と根拠

ORDレコード
ord-b5a7d543e97842baa59caa545ab1d23b
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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