Sodium hydride → HCID 70604950, compound

HRID 616546Notes

Reaction equation

HRID 616546 reaction equation
[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[CH:7]([OH:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].[H-].[Na+].[C:17]([O:22][CH3:23])(=[O:21])[C:18]#[C:19][CH3:20]>C1C=CC=CC=1>[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[CH:7]([O:10]/[C:19](/[CH3:20])=[CH:18]\[C:17]([O:22][CH3:23])=[O:21])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 141019Methyl but-2-ynoateHCID 221822412,6-Diethyl-2,3,6-trimethylpiperidin-4-ol2×

Product 1

HCID 70604950HCID 70604950, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 3.0 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidinol (Compound 1) in 30 ml of benzene was added, in small portions at room temperature, 0.72 g of 50 % sodium hydride. The mixture was then stirred for 30 minutes at room temperature. A solution of 2.2 g of methyl tetrolate in 10 ml of benzene was then added dropwise, with ice-cooling to the mixture and the whole mixture was stirred at room temperature for 64 hours. The mixture was then poured into ice water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulphate. After removing the solvent, the residue was distilled under reduced pressure, giving 3.4 g of Compound 97 as a pale yellow oil (bp 109° - 111° C/0.15 mmHg).

Workup

  1. temperaturecooling to the mixture
  2. stirringthe whole mixture was stirred at room temperature for 64 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulphate
  6. customAfter removing the solvent
  7. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-f5591fb2d3f74dceb82970607b1b9164
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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