Acetic Acid → Dimethyl [3-(3-chlorophenyl)-2-oxopropyl]phosphonate

HRID 478868

反応式

HRID 478868 の反応式
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].[Li]CCCC.C[O:14][C:15](=O)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1.CC(O)=O>C1COCC1>[CH3:4][O:3][P:2]([CH2:1][C:15](=[O:14])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)(=[O:7])[O:5][CH3:6]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 12958Dimethyl methylphosphonateHCID 2733544Methyl 2-(3-chlorophenyl)acetateHCID 178418339Butyllithium

生成物 1

HCID 12989750Dimethyl [3-(3-chlorophenyl)-2-oxopropyl]phosphonate収率 23.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of dimethyl methylphosphonate (17.93 g, 144 mmol) in THF (270 mL) at −78° C. was slowly added n-BuLi (2.5M, 64.2 mL, 160.6 mmol). The reaction mixture was stirred for 1 h and (3-chloro-phenyl)-acetic acid methyl ester (26.93 g, 146 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and was stirred for 24 h. AcOH (15 mL) was added and the volatiles were removed in vacuo. The residue was diluted with CH2Cl2 and the organic solution was washed carefully with saturated aqueous NaHCO3 (3 times). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by medium pressure chromatography (20% EtOAc in hexanes to EtOAc) provided the title compound (9.28 g).

後処理

  1. customat −78° C.
  2. stirringwas stirred for 24 h
  3. customthe volatiles were removed in vacuo
  4. additionThe residue was diluted with CH2Cl2
  5. washthe organic solution was washed carefully with saturated aqueous NaHCO3 (3 times)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by medium pressure chromatography (20% EtOAc in hexanes to EtOAc)

出典と根拠

ORDレコード
ord-56faaacb883d4849b3bc82acb3f8d0cf
出典データセット
uspto-grants-2003_11
特許番号
US06642266B2

関連ノート

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