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

HRID 1262516노트

반응식

HRID 1262516 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c2e2af042c404a7990f4ebdcb3af4449
출처 데이터셋
uspto-grants-1984_06
특허 번호
US04452790

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