1-(Triphenylphosphoranylidene)acetone → HCID 21538222, compound

HRID 1076755Notes

Reaction equation

HRID 1076755 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH:11]=O)=[C:9]([CH3:13])[C:8]([O:14][C:15](=[O:17])[CH3:16])=[C:7]([O:18][CH3:19])[C:6]=1[O:20][CH3:21])(=[O:3])[CH3:2].O=[C:23](C)C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O[CH:49]1[CH2:54][CH2:53][CH2:52][CH2:51][O:50]1)C#C>O1CCOCC1>[C:1]([O:4][C:5]1[C:10]([CH2:11][CH2:23][CH:54]([CH3:49])[CH2:53][CH2:52][CH2:51][OH:50])=[C:9]([CH3:13])[C:8]([O:14][C:15](=[O:17])[CH3:16])=[C:7]([O:18][CH3:19])[C:6]=1[O:20][CH3:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 21538221HCID 21538221, compound

Product 1

HCID 21538222HCID 21538222, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6 parts of 1,4-diacetoxy-2,3-dimethoxy-6-formyl-5-methylbenzene, 12 parts of 2-oxo-1-propylidenetriphenylphosphoran and 500 volume parts of dioxane is stirred under reflux for 17 hours and the reaction mixture is evaporated to dryness. The residue is purified by chromatography on a column of silica gel, whereupon 1,4-diacetoxy-2,3-dimethoxy-5-methyl-6-(3'-oxo-1'-butenyl)-benzene (Formula (VII) wherein R=OCH3 ; OY, OY'=OCOCH3) is obtained as a brown oil. 2 Parts of this product is reacted with 2.77 parts of 2-propargyloxytetrahydropyran, reduced catalytically and hydrolyzed in the same manner as Reference Example 4. The described procedure gives 1,4-diacetoxy-2,3-dimethoxy-5-methyl-6-(6'-hydroxy-3'-methylhexyl)benzene (Formula (IX) wherein R=OCH3 ; OY, OY'=OCOCH3 ; OY"=OH) as a colourless oil.

Workup

  1. temperatureunder reflux for 17 hours
  2. customthe reaction mixture is evaporated to dryness
  3. customThe residue is purified by chromatography on a column of silica gel, whereupon 1,4-diacetoxy-2,3-dimethoxy-5-methyl-6-(3'-oxo-1'-butenyl)-benzene (Formula (VII) wherein R=OCH3 ; OY, OY'=OCOCH3)
  4. customis obtained as a brown oil

Sources & evidence

ORD record
ord-b4632c7b83df4c7fb792279e9b50a7cf
Source dataset
uspto-grants-1976_05
Patent number
US03957836

Reaction notes

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