Potassium Hydroxide → HCID 14515745, compound

HRID 1165896Notes

Reaction equation

HRID 1165896 reaction equation
[CH3:1][C:2](N(C)C)=[O:3].[CH:7]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12](=[CH:13][CH:14]=[CH:15]2)[CH:11]=1)([CH3:9])[CH3:8].P(Cl)(Cl)(Cl)=O.[OH-].[K+]>O>[C:2]([C:13]1[C:12]2[C:16]([CH:17]=[CH:18][CH:19]=[C:10]([CH:7]([CH3:9])[CH3:8])[CH:11]=2)=[CH:15][CH:14]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 24813Phosphorus oxychloride2×HCID 31374Dimethylacetamide2×HCID 156026265-Isopropylazulene

Product 1

HCID 14515745HCID 14515745, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylacetamide (80 ml) solution of the compound (19) (8.41 g), while stirring and cooling with ice, a dimethylacetamide (76 ml) solution of phosphorus oxychloride (POCl3) (92 g) was added dropwise over 40 minutes. After the addition of the POCl3 solution, it was further stirred for 5 hours at room temperature, and then poured into water (800 ml). The solution was made basic (pH 10) by the addition of aqueous potassium hydroxide, and was extracted 5 times with benzene. The benzene solutions were mixed, washed with water and dried. From the benzene solution, the solvent was distilled off to obtain an oily substance. It was purified by silica gel column chromatography (650 g), eluting with benzene. The second-eluted part gave 1-acetyl-7-isopropylazulene (20) (4.29 g, 41%) in a red oily state.

Workup

  1. temperaturecooling with ice
  2. extractionwas extracted 5 times with benzene
  3. additionThe benzene solutions were mixed
  4. washwashed with water
  5. customdried
  6. distillationFrom the benzene solution, the solvent was distilled off
  7. customto obtain an oily substance
  8. customIt was purified by silica gel column chromatography (650 g)
  9. washeluting with benzene

Sources & evidence

ORD record
ord-0b933cbed01d4df3b62c07c553104351
Source dataset
uspto-grants-1990_03
Patent number
US04912134

Reaction notes

Loading…