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

HRID 1187019노트

반응식

HRID 1187019 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 666464675-bromo-3,4-dihydro-1H-isochromene-1-carboxylic acid

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a294a857008548c39ffb10e97dbb2d6b
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673920B2

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