Sodium hydride → tert-butyl (R)-4-(2-methylphenyl)-4-(2-nitro-5-(3-pyridylmethoxy)phenoxy)butanoate

HRID 322974ノート

反応式

HRID 322974 の反応式
F[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[O:5][CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[H-].[Na+].[OH:21][C@@H:22]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])[CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>C1COCC1>[CH3:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[C@H:22]([O:21][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10610687tert-butyl (R)-4-hydroxy-4-(2-methylphenyl)butanoateHCID 220101973-((3-Fluoro-4-nitrophenoxy)methyl)pyridine

生成物 1

HCID 53646282tert-butyl (R)-4-(2-methylphenyl)-4-(2-nitro-5-(3-pyridylmethoxy)phenoxy)butanoate収率 28.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3-(3-Fluoro-4-nitrophenoxymethyl)pyridine (1.53 g) is added to a stirred suspension of sodium hydride (0.48 g, 60% dispersion in mineral oil) in THF (50 mL) at ambient temperature. A solution of tert-butyl (R)-4-hydroxy-4-(2-methylphenyl)butanoate (3.08 g) in THF (30 mL) is added dropwise to the mixture over 2 hours. The reaction mixture is concentrated under reduced pressure and the residue partitioned between water (100 mL) and ethyl acetate (100 mL). The aqueous layer is extracted three times with ethyl acetate (100 mL) and the combined organic phases were dried over magnesium sulphate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with ethyl acetate. Fractions homogeneous in the required product are combined and evaporated to give tert-butyl (R)-4-(2-methylphenyl)-4-(2-nitro-5-(3-pyridylmethoxy)phenoxy)butanoate (0.85 g) as a yellow gum.

後処理

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. extractionThe aqueous layer is extracted three times with ethyl acetate (100 mL)
  4. dry with materialthe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography on silica eluting with ethyl acetate
  8. customevaporated

出典と根拠

ORDレコード
ord-8920c9efbf6b4747b4f5cbe129fa78f5
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

反応ノート

読み込み中…