Sodium Bicarbonate → HCID 68453314, compound

HRID 2233779Notes

Reaction equation

HRID 2233779 reaction equation
[OH:1][C@H:2]([C:5]1[C:6]([F:16])=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][OH:4].O.[C:18]1(C)[CH:23]=CC(S(O)(=O)=O)=C[CH:19]=1.C(=O)(O)[O-].[Na+]>COC(OC)(C)C>[CH3:19][C:18]1([CH3:23])[O:1][C@H:2]([C:5]2[C:6]([F:16])=[C:7]([CH:13]=[CH:14][CH:15]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][O:4]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 68452992HCID 68452992, compound

Product 1

HCID 68453314HCID 68453314, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A 5.71 g portion of ethyl 3-[(1R)-1,2-dihydroxyethyl]-2-fluorobenzoate was dissolved in 30 ml of 2,2-dimethoxypropane, mixed with 476 mg of p-toluenesulfonic acid monohydrate and stirred at room temperature for 30 minutes. This was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate, the organic layer was washed with saturated brine, dried with sodium sulfate and concentrated, and then the thus formed residue was purified by a silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 5.46 g (81%) of ethyl 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluorobenzoate (Reference Example 16-1). FA: 269

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customthe thus formed residue was purified by a silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-3a1e23989a7a4b239af51c5d262b7dfb
Source dataset
uspto-grants-2010_05
Patent number
US07709519B2

Reaction notes

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