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

HRID 365787

Reaction equation

HRID 365787 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-165cb66a52b34f6cbfccbcc9487ca69c
Source dataset
uspto-grants-2000_10
Patent number
US06127540

Linked notes

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