p-Toluenesulfonic acid → HCID 10374796, compound

HRID 2210264Notes

Reaction equation

HRID 2210264 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 (MH30 ); 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-a424354846c64bd592337455c62511f1
Source dataset
uspto-grants-1995_10
Patent number
US05457212

Reaction notes

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