Sodium Bicarbonate → HCID 23130549, compound

HRID 2080123Notes

Reaction equation

HRID 2080123 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[S:9][C:8]([CH:10]2OCC[O:11]2)=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+]>CO.O.Cl>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[S:9][C:8]([CH:10]=[O:11])=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 23130567HCID 23130567, compound

Product 1

HCID 23130549HCID 23130549, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(5-(2-Fluoro-benzyl)-thiophen-2-yl)-[1,3]dioxolane described in Preparation Example 122 (4.33 g, 16.4 mmol) was dissolved in a mixture solvent of methanol (40 mL) and water (10 mL), 1N hydrochloric acid (20 mL) was added thereto, followed by stirring at room temperature for 1 hour. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), and the title compound (3.54 g, 16.1 mmol, 98%) was obtained as a light yellow oil.

Workup

  1. additionwas added
  2. extractionwhich was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-1af4e9316d7045318508f91248bb8181
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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