Acetone → [2-(4,5-Dihydroxy-tetrahydro-furan-2-yl)-vinyl]phosphonic acid diethyl ester

HRID 2191012Notes

Reaction equation

HRID 2191012 reaction equation
[CH2:1]([O:3][P:4]([CH:9]=[CH:10][CH:11]1[O:20][CH:14]2[O:15]C(C)(C)[O:17][CH:13]2[CH2:12]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].Cl.CC(C)=O.C([O-])(O)=O.[Na+]>CC#N>[CH2:1]([O:3][P:4]([CH:9]=[CH:10][CH:11]1[CH2:12][CH:13]([OH:17])[CH:14]([OH:15])[O:20]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 72247323[2-(2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-vinyl]-phosphonic acid diethyl ester

Product 1

HCID 72247331[2-(4,5-Dihydroxy-tetrahydro-furan-2-yl)-vinyl]phosphonic acid diethyl esterYield 111.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 9.6 (3.6 g, 11.76 mmol) in MeCN (40 mL) was treated with 1 N HCl (10 mL) and stirred at 50° C. for 5 h with slow distillation of residual acetone. The solution was cooled to ambient temperature and treated with NaHCO3 (1.0 g) then concentrated in vacuo. The residue was lyophilized overnight and MeOH (20 mL) was added and the solution was filtered. The solution was then co-evaporated with MeCN to afford crude compound 9.7 (3.5 g, >100% yield).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionMeOH (20 mL) was added
  3. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-7b9d3306f13e4964962dcea6e87c1292
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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