p-Toluenesulfonic acid → HCID 10374796, compound

HRID 1086633Notes

Reaction equation

HRID 1086633 reaction equation
O[CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[O:5][C:4]2[CH:10]=[CH:11][S:12][C:3]1=2.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:8][C:6]1([CH3:9])[O:5][C:4]2[CH:10]=[CH:11][S:12][C:3]=2[CH:2]=[CH:7]1

Participants

3

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10241494HCID 10241494, compound

Product 1

HCID 10374796HCID 10374796, compound

Conditions

Temperature
-5 °C

Procedure

A mixture of 5,6-dihydro-7-hydroxy-5,5-dimethyl-7H-thieno [3,2-b]pyran (1.3 g, 7.06 mmol), p-toluenesulfonic acid (0.11 g, 0.58 mmol) and ground molecular sieves (1.3 g) was stirred at -5° C. for 1.5 h. The mixture was washed with 1.0N aqueous sodium hydroxide and dried over magnesium sulfate. The solvent was evaporated in vacuo to give the product, 1.17 g (99%), as a red oil: IR (neat): 2976, 1504 and 1531 cm-1 ; MS: m/z 167 (MH+); 1H NMR (CDCl3): δ1.45(s, 6H), 5.27(d, J=9.8 Hz, 1H), 6.30 (d, J=9.8 Hz, 1H), 6.60(d, J=5.3 Hz, 1H) and 6.99(d, J=5.3 Hz, 1H). This oil was used without further purification in the next step.

Workup

  1. washThe mixture was washed with 1.0N aqueous sodium hydroxide
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customto give the product, 1.17 g (99%)
  5. customThis oil was used without further purification in the next step

Sources & evidence

ORD record
ord-0582a7f15edb4d90badd518d5980f406
Source dataset
uspto-grants-1991_07
Patent number
US05030736

Reaction notes

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