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

HRID 1187019ノート

反応式

HRID 1187019 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]([O:14]C)=[O:13].O[Li].O>CO.C1COCC1.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][O:6][CH:7]2[C:12]([OH:14])=[O:13]

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 66646338methyl 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylate

生成物 1

HCID 666464675-bromo-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 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylate (12.1 g, 42.4 mmol) in 200 mL of MeOH/THF/H2O (2/2/1) was added LiOH.H2O (5.34 g, 0.127 mol), and the mixture was stirred at ambient temperature for 30 min. The solvents were removed under vacuum, and the residue was added 100 mL of water and extracted with ether. The aqueous layer was then acidified with 4 N HCl to pH=4˜5 in ice bath, and extracted with EtOAc. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated to afford 5-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid.

後処理

  1. customThe solvents were removed under vacuum
  2. additionthe residue was added 100 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-a294a857008548c39ffb10e97dbb2d6b
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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