Benzyl Alcohol → (+/-)-2-[[Phenylmethoxy(4-phenylbutyl)phosphinyl]oxy]propionic acid, ethyl ester

HRID 1262516ノート

反応式

HRID 1262516 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11](=[O:14])([OH:13])[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.[C:28]([O:33][CH2:34][CH3:35])(=[O:32])[CH:29]([CH3:31])O.[CH2:36](O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl.C1C=CC=CC=1>[C:37]1([CH2:36][O:14][P:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([O:13][CH:29]([CH3:31])[C:28]([O:33][CH2:34][CH3:35])=[O:32])=[O:12])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

8

反応物 5

HCID 244Benzyl AlcoholHCID 7344Ethyl LactateHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 13687984(4-Phenylbutyl)phosphonic acid

生成物 1

HCID 86739440(+/-)-2-[[Phenylmethoxy(4-phenylbutyl)phosphinyl]oxy]propionic acid, ethyl ester収率 60%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 4-phenylbutyl phosphonic acid from Part A (0.70 g, 3.27 mmole), benzene (10 ml), and PCl5 (1.36 g, 6.54 mmole) was refluxed under argon for 30 minutes. The benzene and POCl3 were removed in vacuo and the residue taken up in CH2Cl2 (5 ml). After cooling to 0° C. (ice-bath), triethylamine (1.3 ml, 9.39 mmole) was added followed by dropwise treatment with d,1 ethyl lactate (0.39 ml, 3.3 mmole) in CH2Cl2 (3 ml) over a 5 minute period. After 1 hour benzyl alcohol (0.35 ml, 3.3 mmole) in CH2Cl2 (3 ml) was added dropwise over 2 minutes, the ice-bath removed, and the reaction mixture allowed to stir for 2 hours. The reaction mixture was diluted with EtOAc then washed with H2O, 5% KHSO4, saturated NaHCO3, brine, dried (MgSO 4), and evaporated. The residue (1.3 g) was chromatographed on silica (70 g) eluting with 2/1 hexane/EtOAc to obtain the title compound (0.80 g, 1.98 mmole; 60% yield) as an oil.

後処理

  1. temperaturewas refluxed under argon for 30 minutes
  2. customThe benzene and POCl3 were removed in vacuo
  3. additionwas added
  4. customthe ice-bath removed
  5. additionThe reaction mixture was diluted with EtOAc
  6. washthen washed with H2O, 5% KHSO4, saturated NaHCO3, brine
  7. dry with materialdried (MgSO 4)
  8. customevaporated
  9. customThe residue (1.3 g) was chromatographed on silica (70 g)
  10. washeluting with 2/1 hexane/EtOAc

出典と根拠

ORDレコード
ord-c2e2af042c404a7990f4ebdcb3af4449
出典データセット
uspto-grants-1984_06
特許番号
US04452790

反応ノート

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