HCID 10380396, compound → HCID 54258336, compound

HRID 1494132Notes

Reaction equation

HRID 1494132 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 0.58 M 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 minutes, 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 hours. 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-tetra- hydropyranyloxy)-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 hours
  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-fdd1ad115de24d638bc6ce6b77784743
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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