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

HRID 365786

Reaction equation

HRID 365786 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]CC(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 208273-Bromo-1,2-propanediolHCID 82071Diethyl (2,2-diethoxyethyl)phosphonateHCID 516892Sodium Bicarbonate

Product 1

HCID 56632209Trans 4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-DioxolaneYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of diethylphosphonoacetaldehyde diethylacetal (15.00 g, 59.0 mmol) and 3-bromo-1,2-propanediol (11.00 g, 71.0 mmol, 1.2 eq.) in toluene (60 mL) was added pTSA (few cristals). The mixture was stirred at reflux for 72 hr and was cooled to room temperature. A saturated solution of sodium bicarbonate was added and the aqueous phase was extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude material was pure by TLC and NMR and gave 17.93 g of the compound in a 96% yield.

Workup

  1. temperatureat reflux for 72 hr
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-296f24d0051443a9b8e73d11e9abf7fb
Source dataset
uspto-grants-2000_10
Patent number
US06127540

Linked notes

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