Dimethyl Sulfoxide → HCID 5371891, compound

HRID 1741675Notes

Reaction equation

HRID 1741675 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=O.CS(C)=[O:13].[NH4+].[Cl-].[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[CH:9]=[CH:18]/[C:19]([O:20][CH2:21][CH3:17])=[O:13]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8028Tetrahydrofuran2×HCID 142732-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 5371891HCID 5371891, compound

Procedure

An 80% dipersion of sodium hydride in oil (1.31 g, 43.5 mmol, 1.15 eq) was added portionwise (~10 min) to a solution of triethylphosphonoacetate (8.26 mL, 41.6 mmol, 1.1 eq) in dry THF (160 mL) at 0° C. After 20 min., a solution of 2-pyridinecarboxaldehyde (4.05 g, 37.8 mmol) in dry THF (80 mL) was added dropwise (20 min.) at 0° C. Dry DMSO (20 mL) was added to dissolve solids formed during the addition. After 15 min., at 0° C., the mixture was poured into a cold saturated solution of NH4Cl. The layers were separated and the aqueous phase was extracted with EtOAc (3x). The organic phase was concentrated and combined with the EtOAc extracts. Conventional aqueous workup, followed by chromatography on silica using EtOAc/hexane (1:4→1:3) as eluent afforded 5.86 g of the title compound.

Workup

  1. dissolutionto dissolve solids
  2. customformed during the addition
  3. waitAfter 15 min.
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with EtOAc (3x)
  6. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-17ca707dec91468e9fa39044f3d63031
Source dataset
uspto-grants-1994_08
Patent number
US05334597

Reaction notes

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