Toluene → HCID 67806046, compound

HRID 1975078Notes

Reaction equation

HRID 1975078 reaction equation
C([O:5][C:6]1C(C(=O)C=C(C)C)=C[S:8][CH:7]=1)(C)(C)C.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1.[C:28]1([CH3:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH3:34][C:28]1([CH3:29])[C:33]2[CH:6]([O:5][CH:30]=[CH:31][CH:32]=2)[C:7](=[O:24])[S:8]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 15643886HCID 15643886, compound

Product 1

HCID 67806046HCID 67806046, compound

Procedure

A solution of 3-t-butoxy-4-(3-methyl-1-oxo-2-buten-1-yl) thiophene (12.2 g, 51.2 mmol) and p-toluenesulfonic acid (0.5 g) in toluene was heated to reflux for 2 h. The solvent was evaporated in vacuo and the residue was purified by flash chromatography using 25% hexane in dichloromethane as the eluant to give 24 as a waxy tan solid, 5.9 g (63%); mp 42°-45 0C; IR(neat): 2977, 1692 and 1554 cm-1 ; MS: m/z 183 (MH+); 1H NMR(CDCl3): δ 1.44 (s,6H), 2.62 (s, 2H), 6.43 (d, J=3.3 Hz, 1H) and 8.00 (d, J=3.3 Hz, 1H).

Workup

  1. temperatureto reflux for 2 h
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d588930443eb486a962f94f5150f3814
Source dataset
uspto-grants-1994_02
Patent number
US05284857

Reaction notes

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