p-Toluenesulfonic acid → (2S,4R)-4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane

HRID 618853

반응식

HRID 618853 반응식
[CH2:1]([O:3][CH:4]([O:14][CH2:15][CH3:16])[CH2:5][P:6]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])=[O:7])C.[Br:17]C[C@H](O)CO.CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:17][CH2:16][C@H:15]1[CH2:1][O:3][C@H:4]([CH2:5][P:6]([O:8][CH2:9][CH3:10])([O:11][CH2:12][CH3:13])=[O:7])[O:14]1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 82071Diethyl (2,2-diethoxyethyl)phosphonateHCID 516892Sodium BicarbonateHCID 2733893(2R)-3-Bromo-1,2-propanediol

생성물 1

HCID 53652584(2S,4R)-4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane수율 97%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of diethylphosphonoacetaldehyde diethylacetal (4.20 g, 16.5 mmol) and (2R)-3-bromo-1,2-propanediol (example 90) (3.00 g, 19.4 mmol, 1.2 eq.) in toluene (30 mL) was added PTSA (few crystals). The mixture was stirred at reflux for 50 hr. After, the solution was cooled to room temperature, and a saturated solution of sodium bicarbonate was added, and the aqueous phase was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude material was pure by TLC and NMR, and gave 5.06 g of the compound in a 97% yield.

후처리

  1. temperatureat reflux for 50 hr
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-6dfae0c5299f4d2dbed787f003175797
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05955610

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