Ethyl Glycolate → HCID 66864346, compound

HRID 2093082Notes

Reaction equation

HRID 2093082 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].[H-].[Na+].Cl[C:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][C:12]=1[CH:27]=O>C1COCC1>[CH3:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([N:14]2[CH2:15][CH2:16][C:11]3[O:3][C:2]([C:1]([O:5][CH2:6][CH3:7])=[O:4])=[CH:27][C:12]=3[CH2:13]2)(=[O:18])=[O:19])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 86650192HCID 86650192, compound

Product 1

HCID 66864346HCID 66864346, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl glycolate (1 eq) in THF was added sodium hydride (2.5 eq) at 0° C. and the reaction mixture was stirred for 1 h 4-chloro-1-[(4-methylphenyl)sulfonyl]-1,2,5,6-tetrahydropyridine-3-carbaldehyde (1 eq) obtained in step II of example 200 in THF was added at 0° C. and was refluxed for 2 h. Reaction was quenched with water and extracted with ethyl acetate, organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the ethyl 5-[(4-methylphenyl)sulfonyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine-2-carboxylate.

Workup

  1. additionwas added at 0° C.
  2. temperaturewas refluxed for 2 h
  3. customReaction
  4. customwas quenched with water
  5. extractionextracted with ethyl acetate, organic layer
  6. customwas separated
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto afford crude product, which
  10. customon purification by column chromatography

Sources & evidence

ORD record
ord-36e67a9784644bceb4b689c6f734b535
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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