Sodium hydride → HCID 54396318, compound

HRID 248928Notes

Reaction equation

HRID 248928 reaction equation
[H-].[Na+].[CH2:3]([C:7]1([CH:19]=CC(C)=CC1)S(C[N+]#[C-])(=O)=O)[CH2:4][CH2:5][CH3:6].[CH:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:21][CH:22]=[CH2:23].[Cl-].[NH4+:29]>CCOCC.CS(C)=O>[CH2:3]([C:7]1[NH:29][CH:23]=[C:22]([CH:21]=[CH:20][C:24]([O:26][CH3:27])=[O:25])[CH:19]=1)[CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 736882,4-Pentadienoic acid, methyl esterHCID 86746855HCID 86746855, compound

Product 1

HCID 54396318HCID 54396318, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) suspension of NaH (5.4 g, 60% suspension in mineral oil) in anhydrous ether (180 ml) was added dropwise a mixture of 1-n-butyltosylmethylisocyanide (29 g) and methyl butadienecarboxylate (;2.2 ml) in anhydrous ether (180 ml) and dry dimethyl sulfoxide (90 ml) under an inert atmosphere. The reaction mixture was first stirred at 0° C. for 1 hour and then slowly brought to room temperature and the stirring continued for an additional 6 hours. The reaction mixture was then cooled to 0° C. and cautiously poured onto aqueous saturated ammonium chloride solution (200 ml). The organic layer was separated, and the aqueous layer was thoroughly extracted with ethyl acetate. The combined ether and ethyl acetate extracts were sequentially washed with saturated ammonium chloride solution in cold water, and then brine, and dried with magnesium sulfate. The solvent was removed under vacuum and the residue purified by column chromatography on silica gel, eluting with 15% ethyl acetate/hexane, to afford methyl 3-[ 2-(n-butyl)pyrrol-4-yl]acrylate as a yellow oil (15.32 g), a compound of Formula (AE), which crystallized on standing to a solid, m.p. 65°-67° C.

Workup

  1. additionwas added dropwise
  2. customslowly brought to room temperature
  3. waitthe stirring continued for an additional 6 hours
  4. temperatureThe reaction mixture was then cooled to 0° C.
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was thoroughly extracted with ethyl acetate
  7. washThe combined ether and ethyl acetate extracts were sequentially washed with saturated ammonium chloride solution in cold water
  8. dry with materialbrine, and dried with magnesium sulfate
  9. customThe solvent was removed under vacuum
  10. customthe residue purified by column chromatography on silica gel
  11. washeluting with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-50b43c9cd24548a1b3e99cc32dbe9c60
Source dataset
uspto-grants-1993_05
Patent number
US05212195

Reaction notes

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