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CID 6327156 → (R)-2-(2,3-dichlorophenyl) propanoic acid

HRID 64242
ノート
印刷プレビュー

反応式

HRID 64242 の反応式
C([C@@H]1COC(=O)N1[C:14](=[O:25])[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[Cl:24])[CH3:16])C1C=CC=CC=1.[Li].[Li+].[O-:28][O-]>C1COCC1.O>[Cl:24][C:18]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:17]=1[C@@H:15]([CH3:16])[C:14]([OH:25])=[O:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6327156CID 6327156HCID 90041040HCID 90041040、化合物

生成物 1

HCID 34175473(R)-2-(2,3-dichlorophenyl) propanoic acid収率 86.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of compound 20 (160 mg, 0.42 mmol) in THF (5 mL) and water at 0° C., was added a solution of lithium peroxide (prepared by adding 30% hydrogen peroxide (2.9 mL, 2.10 mmol) to lithium hydroxide (17.6 mg, 0.41 mmol) in water (0.679 mL)) dropwise. The mixture was stirred for 0° C. for 1h, quenched with sat.Na2SO3 (1.28 mL), solvent was removed in vacuo. The mixture was diluted with water and aqueous solution was extracted with DCM twice. The aq.layer was acidified with Conc.HCl and extracted with EtOAc twice. Combined organic layers were washed with brine and dried over MgSO4, concentrated. Purified by column chromatography (EtOAc/n-Hexane 40:60) to afforded compound 21 (80 mg, 86.9%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 1.51 (d, J=7.2 Hz, 3H), 4.27 (q, J=6.8 Hz, 1H), 7.16-7.24 (m, 2H), 7.37 (d, J=7.6 Hz, 1H)).

後処理

  1. customquenched
  2. customNa2SO3 (1.28 mL), solvent was removed in vacuo
  3. additionThe mixture was diluted with water and aqueous solution
  4. extractionwas extracted with DCM twice
  5. extractionHCl and extracted with EtOAc twice
  6. washCombined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customPurified by column chromatography (EtOAc/n-Hexane 40:60)

出典と根拠

ORDレコード
ord-19bffd29974447f38674480a3afbc3de
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447134B2

反応ノート

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