Sodium Hydroxide → HCID 86692511, compound

HRID 1748565Notes

Reaction equation

HRID 1748565 reaction equation
C[O:2][C:3]([C:5]1([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([Br:18])=[CH:13][N:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>O1CCCC1.CO>[Br:18][C:14]1[CH:15]=[C:16]([CH3:17])[C:11]([C:5]2([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)=[N:12][CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86692510HCID 86692510, compound

Product 1

HCID 86692511HCID 86692511, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid methyl ester (745 mg) in tetrahydrofuran (5 ml) and methanol (5 ml) was added 4 N aqueous solution of sodium hydroxide (5 ml) at room temperature, and stirred overnight. After completion of the reaction, the organic solvent was evaporated, diluted with 1 N aqueous solution of sodium hydroxide and water, diethyl ether was added thereto, and the aqueous layer was separated. The aqueous layer was ice-cooled, concentrated hydrochloric acid was added thereto to adjust the layer to pH 4, extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to give 4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid (421 mg) as a white solid. MS (ESI) m/z: 300, 302 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated
  3. additiondiluted with 1 N aqueous solution of sodium hydroxide and water, diethyl ether
  4. additionwas added
  5. customthe aqueous layer was separated
  6. temperaturecooled
  7. additionconcentrated hydrochloric acid was added
  8. extractionextracted with chloroform
  9. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9f08fd6aa85a479c90784c4a0a355d84
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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