HCID 10380396, compound → HCID 54258336, compound

HRID 465592Notes

Reaction equation

HRID 465592 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[K].[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH:12]=1>C1(C)C=CC=CC=1>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][C:20]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[CH:31][C:26]([O:25][CH2:24][CH3:23])=[O:27])[CH:12]=1

Participants

4

Reactant 2

HCID 10380396HCID 10380396, compoundHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt

Product 1

HCID 54258336HCID 54258336, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 5.74 ml (93.33 mmol) of 0.58M potassium hexamethyldisilazane in toluene is added dropwise 0.66 ml triethyl phosphonoacetate resulting in a yellow gelatinous mixture. This reaction mixture is stirred at room temperature for 25 min, a solution of 0.5 g (1.66 mmol) 1-(3-pyridyl)-4-oxo-8-(2-tetrahydropyranyloxy)-octane in 3 ml toluene is added and the mixture is refluxed for 15 h. The reaction mixture is cooled to room temperature, quenched with 5 ml saturated aqueous ammonium chloride solution and extracted with ethyl acetate twice. The combined organic phase is washed with water and brine, dried, filtered, and concentrated to give a brown oil which is purified by chromatography using 1:1 ethyl acetate/hexane to yield ethyl 3-[3-(3-pyridyl)propyl]-7-(2-tetrahydropyranyloxy)-hept-2-enoate as a mixture of cis and trans isomers; NMR (CDCl3): delta 5.7 (s,1H), 4.2 (q,2H), 1.3 (t,3H).

Workup

  1. temperaturethe mixture is refluxed for 15 h
  2. temperatureThe reaction mixture is cooled to room temperature
  3. customquenched with 5 ml saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate twice
  5. washThe combined organic phase is washed with water and brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown oil which
  10. customis purified by chromatography

Sources & evidence

ORD record
ord-568797095ee1407688d9403ae5924f28
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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