HCID 22969121, compound → HCID 22969120, compound

HRID 1278850Notes

Reaction equation

HRID 1278850 reaction equation
[CH:1]([O:4][P:5]([CH:11]1[CH:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][CH:14]2[CH:13]([CH2:21][O:22]C(=O)C)[O:12]1)([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])([CH3:3])[CH3:2]>CO.C[O-].[Na+]>[CH:1]([O:4][P:5]([CH:11]1[CH:15]2[CH:14]([O:18][C:17]([CH3:19])([CH3:20])[O:16]2)[CH:13]([CH2:21][OH:22])[O:12]1)(=[O:6])[O:7][CH:8]([CH3:10])[CH3:9])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22969121HCID 22969121, compound

Product 1

HCID 22969120HCID 22969120, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

Acetic acid 6-(diisopropoxy-phosphoryl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (467 mg, 1.22 mmol) in dry methanol (10 mL) and methanolic sodium methoxide (0.1M, 1 mL) was stirred at RT for 0.5 h. Dowex acidic resin was added until neutral pH was attained, the reaction mixture filtered and concentrated to give (6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-phosphonic acid diisopropyl ester as a colorless syrup (409 mg, 99%).

Workup

  1. additionDowex acidic resin was added until neutral pH
  2. filtrationthe reaction mixture filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a30b3d39c5d44932b427040a40689135
Source dataset
uspto-grants-2002_09
Patent number
US06444656B1

Reaction notes

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