Piperidine → HCID 21440282, compound

HRID 328752

Reaction equation

HRID 328752 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12](=[O:17])[CH2:13]S(C)=O.[CH:18]([CH:20]1[CH2:22][CH:21]1[C:23]([O:25][CH2:26][CH3:27])=[O:24])=O.N1CCCCC1>C1(C)C=CC=CC=1>[O:17]=[C:12]1[CH:13]=[C:18]([CH:20]2[CH2:22][CH:21]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:1][C:2]2[C:11]3[C:6]([CH:5]=[CH:4][C:3]1=2)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 8082PiperidineHCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 12715524HCID 12715524, compound

Product 1

HCID 21440282HCID 21440282, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 12.4g of 1'-hydroxy-2-(methylsulfinyl)-2'-acetonaphthone, 7.1g of ethyl 2-formyl-1-cyclopropane carboxylate, 250ml of toluene and 0.5ml of piperidine was refluxed for 8 hrs. The toluene was then removed under reduced pressure, and the oily residue was recrystallized from Skelly B with the aid of charcoal, mp. 106°-07.5°; yield 6.5g (42%); λ max mμ (ε) 219 (50,000), 259 (36,800), 327 (3,990), 341 (4,100); ν max 760 (m), 825 (ms), 1195 (s), 1640 (s), 1650 (s), 1730 (s) cm-1.

Workup

  1. temperaturewas refluxed for 8 hrs
  2. customThe toluene was then removed under reduced pressure
  3. customthe oily residue was recrystallized from Skelly B with the aid of charcoal, mp. 106°-07
  4. custom5°

Sources & evidence

ORD record
ord-5e5375d87fc248c5bdab84e5a8b04f9c
Source dataset
uspto-grants-1977_04
Patent number
US04018798

Linked notes

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