p-Toluenesulfonic acid → HCID 57001676, compound

HRID 264552Notes

Reaction equation

HRID 264552 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[CH3:12][CH:13](O)[CH:14]=[CH2:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>COC(OC)(C)C.C1(C)C=CC=CC=1>[CH2:12]([CH:2]1[CH2:3][C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[S:1]1)[CH:13]=[CH:14][CH3:15]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 19048Thiochroman-4-one

Product 1

HCID 57001676HCID 57001676, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 64952,2-DimethoxypropaneSolvent

Procedure

A solution of 23.9 g of 4-thiochromanone, 30 ml of 3-buten-2-ol and 240 mg of p-toluenesulfonic acid in 30 ml of 2,2-dimethoxy-propane and 240 ml of anhydrous toluene was boiled under reflux for 20 hours. The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 5:1). 15.3 g (48%) of (RS)-2-(2-buten-1-yl)-4-thiochromanone were obtained as a yellow oil.

Workup

  1. temperatureunder reflux for 20 hours
  2. concentrationThe reaction mixture was subsequently concentrated in a vacuum
  3. custompurified by column chromatography on silica gel (hexane/diethyl ether 5:1)

Sources & evidence

ORD record
ord-579e03b2393a4366bed40e1392d8f8f2
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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