Lithium Hydroxide → 5-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid

HRID 448926ノート

反応式

HRID 448926 の反応式
C(OC(CCC[O:11][C:12](=[O:32])[C:13]1[CH:18]=[C:17]([Br:19])[C:16]([Cl:20])=[CH:15][C:14]=1[O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=O)(C)(C)C.[Li+].[OH-].OS([O-])(=O)=O.[Na+]>C1COCC1>[Br:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]([O:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])=[C:13]([CH:18]=1)[C:12]([OH:32])=[O:11]

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 686035915-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 3-tert-butoxycarbonyl-propyl ester

生成物 1

HCID 686032665-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid収率 41.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 5-bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 3-tert-butoxycarbonyl-propyl ester (8.2 g, 15.3 mmol) and LiOH (19.1 mL, 4 N, 76.6 mmol) in THF (150 mL) was stirred at rt for 16 hrs. The mixture was acidified by saturated NaHSO4 (50 mL) and extracted with ethyl acetate. The ethyl acetate layer was dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash chromatography (eluting with 50% ethyl acetate in hexane), followed by crystallization in hexane/ethyl acetate (10/1) to afford 5-bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid as white crystals (2.5 g). MS [M-(iso-butene+OH)]+: 320.8; tR=2.38 min. (method 1)

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via silica gel flash chromatography (eluting with 50% ethyl acetate in hexane)
  6. customfollowed by crystallization in hexane/ethyl acetate (10/1)

出典と根拠

ORDレコード
ord-a81ec6164d6c49c99c01e762ea4fc8ff
出典データセット
uspto-grants-2013_07
特許番号
US08481738B2

反応ノート

読み込み中…