p-Toluenesulfonic acid → HCID 53765700, compound

HRID 1701421Notes

Reaction equation

HRID 1701421 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C([O:9][CH2:10][C:11]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:12][CH2:13][CH2:14][C:15](=O)[CH3:16])(=O)C.[OH-].[Na+].[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1.[O:37]1CC[CH2:39][CH2:38]1>CO>[OH:9][CH2:10][C:11]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:16])[CH3:26])=[CH:18][CH2:19][CH2:20][C:21]([CH3:22])=[CH:23][CH2:1][CH2:2][C:3]([CH3:4])=[CH:39][CH2:38][OH:37]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 53845978HCID 53845978, compoundHCID 178418339Butyllithium

Product 1

HCID 53765700HCID 53765700, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 120 ml of anhydrous tetrahydrofuran was suspended 23.1 g of (E)-4-methyl-6-(2'-tetrahydropyranyloxy)-4-hexen-1-yltriphenylphosphonium iodide. In the same manner as in Example 2-(1), the equimolar amount of n-butyllithium and 7.2 g of 6-acetoxymethyl-10-methyl-5,9-undecadien-2-one prepared in Referential Examples 4 and 5 were added to the suspension, and the Wittig reaction was carried out. The product was hydrolyzed with 70 ml of an alcoholic sodium hydroxide (5%) and treated overnight with methanol containing 100 mg of p-toluenesulfonic acid at room temperature. This was then purified by the silica gel (100 g) column chromatography to yield 3.7 g of the desired product, which was a mixture of the (E,E,E), (E,Z,Z), (E,Z,E) and (E,E,Z) isomers.

Workup

  1. additionwere added to the suspension
  2. customthe Wittig reaction
  3. customThis was then purified by the silica gel (100 g) column chromatography

Sources & evidence

ORD record
ord-4a13bb1844834dfc9eaa47941419829c
Source dataset
uspto-grants-1980_03
Patent number
US04192953

Reaction notes

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