Water → Dimethyl(2-oxo-4-phenylbutyl)phosphonate

HRID 449167

反応式

HRID 449167 の反応式
[CH3:1][O:2][P:3]([CH3:7])(=[O:6])[O:4][CH3:5].[CH2:8]([Li])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:15][CH2:16][C:17]1C=CC=C(OC(CC)=O)C=1.[OH2:28]>C1COCC1>[CH3:1][O:2][P:3]([CH2:7][C:8](=[O:28])[CH2:9][CH2:10][C:11]1[CH:17]=[CH:16][CH:15]=[CH:13][CH:12]=1)(=[O:6])[O:4][CH3:5]

参加物

6

反応物 4

HCID 962WaterHCID 12958Dimethyl methylphosphonateHCID 2734115Propionic acid, 3-ethylphenyl esterHCID 178506865HCID 178506865、化合物

生成物 1

HCID 2733973Dimethyl(2-oxo-4-phenylbutyl)phosphonate収率 89.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 68 g of methyl-phosphonic-acid dimethyl ester (MW=124.8; 1.6 eq.) in 325 mL of THF was added 218 mL of n-hexyllithium (2.5M in hexane; 1.6 eq.) at −80° C. The mixture was stirred for 30 min and a solution of 60 g of ethyl-3-phenyl propionate (MW=178.23, d=1.01, 1.0 eq.) in 90 mL of THF was added. The mixture was allowed to warm to ambient temperature and 150 mL of water were added. After separation of the layers the organic layer was extracted twice with water. The pH value of the combined aqueous layers was adjusted to pH=2 with 5M HCl and then extracted twice with DCM. Removal of the organic solvents under reduced pressure gave 89 g of the title compound (Assay: 86.8%; Yield=89.7%). It is not necessary to dry to completion, a 50 w % solution in MED is also suitable for the next step.

後処理

  1. customAfter separation of the layers the organic layer
  2. extractionwas extracted twice with water
  3. extractionextracted twice with DCM
  4. customRemoval of the organic solvents under reduced pressure

出典と根拠

ORDレコード
ord-2d379244b2b54006aaa262f1dbcaf58b
出典データセット
uspto-grants-2013_07
特許番号
US08481758B2

関連ノート

読み込み中…