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

HRID 459002

反応式

HRID 459002 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.C(O)(=O)C>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. Acetic acid (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-2a19f2ecff17431880410c53b34f053b
出典データセット
uspto-grants-2007_03
特許番号
US07192979B2

関連ノート

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