Butanal, 4-[(tetrahydro-2H-pyran-2-yl)oxy]- → 2-{[5-(4-Chlorophenyl)pent-4-en-1-yl]oxy}oxane

HRID 1381368

Reaction equation

HRID 1381368 reaction equation
C([Li])CCC.[Cl-].[Cl:7][C:8]1[CH:33]=[CH:32][C:11]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:10][CH:9]=1.[O:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]1[O:40][CH2:41][CH2:42][CH2:43][CH:44]=O>O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[CH:44][CH2:43][CH2:42][CH2:41][O:40][CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39][O:34]2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 551206Butanal, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-HCID 2733546(4-Chlorobenzyl)triphenylphosphonium chlorideHCID 178418339Butyllithium

Product 1

HCID 544213722-{[5-(4-Chlorophenyl)pent-4-en-1-yl]oxy}oxaneYield 47.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an argon atmosphere, butyllithium (10%; 37 ml) was added dropwise to a suspension of (4-chlorobenzyl)triphenylphosphonium chloride (24 g) in tetrahydrofuran (70 ml) with ice-cooling and stirring. After stirring at the same temperature for 30 minutes, a solution of 4-tetrahydropyranyloxy-1-butanal (9 g) in tetrahydrofuran (30 ml) was added dropwise, and the mixture was stirred at room temperature for 2 hours. The tetrahydrofuran was distilled off under reduced pressure and water was added to the residue, followed by extraction with petroleum ether. After washing with water and drying over magnesium sulfate, the solvent was distilled off, and the residue was subjected to silica gel column chromatography, elution being carried out with chloroform to give 1-(4-chlorophenyl)-5-(2-tetrahydropyranyloxy)-1-pentene (7 g) as a light-yellow oil.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at the same temperature for 30 minutes
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. distillationThe tetrahydrofuran was distilled off under reduced pressure and water
  5. additionwas added to the residue
  6. extractionfollowed by extraction with petroleum ether
  7. washAfter washing with water
  8. dry with materialdrying over magnesium sulfate
  9. distillationthe solvent was distilled off
  10. washthe residue was subjected to silica gel column chromatography, elution

Sources & evidence

ORD record
ord-a1407fe3feb24b278729b8e8236e9ebe
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Linked notes

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