4-Toluenesulfonyl chloride → 2-Benzyloxymethyl-3-diethylphosphonomethoxy-1-(p-toluenesulfonyloxy)propane

HRID 266231노트

반응식

HRID 266231 반응식
[CH2:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][O:12][S:37]([C:34]1[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=1)(=[O:39])=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 537262552-Benzyloxymethyl-3-diethylphosphonomethoxy-1-propanol

생성물 1

HCID 544722702-Benzyloxymethyl-3-diethylphosphonomethoxy-1-(p-toluenesulfonyloxy)propane수율 81.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of 2-benzyloxymethyl-3-diethylphosphonomethoxy-1-propanol (0.25 g, 0.72 mmol) in 5 mL of CH2Cl2 was cooled to 0° C. and treated with triethylamine (0.22 g, 2.16 mmol). A solution of p-toluenesulfonyl chloride (0.151 g, 0.79 mmol) in 2 mL of CH2Cl2 was added next and the reaction mixture allowed to warm gradually to room temperature. After 14 hours at room temperature, the mixture was diluted with CH2Cl2 and washed with two portions of 10% aqueous HCl and saturated sodium chloride solution, dried over MgSO4, filtered, and concentrated to give an orange oil. Purification by column chromatography on silica gel (1-3% ethanol in ethyl acetate) provided 0.295 g of 2-benzyloxymethyl-3-diethylphosphonomethoxy-1-(p-toluenesulfonyloxy)propane as a pale yellow oil.

후처리

  1. washwashed with two portions of 10% aqueous HCl and saturated sodium chloride solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an orange oil
  6. customPurification by column chromatography on silica gel (1-3% ethanol in ethyl acetate)

출처 및 근거

ORD 기록
ord-c79a50b82dcf45c2930754bc3992feaa
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650510

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