p-Toluenesulfonic acid → HCID 10374796, compound

HRID 257206Notes

Reaction equation

HRID 257206 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 (1.3g, 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 1.0 N 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 1.0 N 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-27cdb400c59f453fa15b95d2dd46e225
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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