Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 23051848, compound

HRID 1651363Notes

Reaction equation

HRID 1651363 reaction equation
C(OC([O:6][CH2:7][C:8]#[C:9][C:10](=[O:25])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=1)C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C.O1CCCC1.O>[OH:6][CH2:7][C:8]#[C:9][C:10](=[O:25])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 23051851HCID 23051851, compound

Product 1

HCID 23051848HCID 23051848, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 4 g (11.5 mmol) of (E)-6-(1-ethoxy-ethoxy)-1-(3,4,5-trimethoxyphenyl)-1-hexen-4-yn-3-one in 40 ml of ethanol/tetrahydrofuran (1:1) was treated at room temperature with 0.4 g (1.6 mmol) of pyridinium (toluene-4-sulphonate) and was stirred at room temperature for 20 hours. The reaction mixture was diluted with water and extracted twice with ether. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 200 g of silica gel (elution agent methylene chloride/ether 4:1) and was subsequently crystallized from methylene chloride/ether. There was obtained (E)-6-hydroxy-1-(3,4,5-trimethoxyphenyl)-1-hexen-4-yn-3-one of melting point 113°-115°.

Workup

  1. extractionextracted twice with ether
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on 200 g of silica gel (elution agent methylene chloride/ether 4:1)
  5. customwas subsequently crystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-e3b41b03a779405b84b6ceab9b58707d
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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