Lithium hydroxide, monohydrate → 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid

HRID 1187140ノート

反応式

HRID 1187140 の反応式
[Br:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([O:14]C)=[O:13])[O:7][CH2:6][CH2:5]2.O[Li].O>CO.C1COCC1.O>[Br:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]([OH:14])=[O:13])[O:7][CH2:6][CH2:5]2

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 67516849methyl 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylate

生成物 1

HCID 666463356-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

To a solution of methyl 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylate (650 mg, 2.06 mmol) in 20 mL of MeOH/THF/H2O (2/2/1) was added LiOH.H2O (347 mg, 8.25 mmol), and the mixture was stirred at ambient temperature overnight. The solvents were removed under vacuum, and the residue was added 50 mL of water and extracted with ether. The aqueous layer was then acidified with 4 N HCl to pH=3 in ice bath, and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated to give 6-bromo-5-(methyloxy)-3,4-dihydro-1H-isochromene-1-carboxylic acid.

後処理

  1. customThe solvents were removed under vacuum
  2. additionthe residue was added 50 mL of water
  3. extractionextracted with ether
  4. extractionextracted with EtOAc
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ca870f29e25b4bec9798cbab4e724775
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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