Hexane → Thiophene, 3-methoxy-2-(methylthio)-

HRID 649168Notes

Reaction equation

HRID 649168 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][CH:4]=1.CCCCCC.C([Li])CCC.[CH3:19][S:20]SC>C(OCC)C.O>[CH3:19][S:20][C:4]1[S:5][CH:6]=[CH:7][C:3]=1[O:2][CH3:1]

Participants

7

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 21 g of 3-methoxythiophene in diethyl ether at -40° C. was added 115 ml of a 1.6 molar hexane solution of n-butyllithium. The mixture was warmed slowly over 10 minutes to 0° C., then refluxed for 1 hour, was cooled to -78° C. and a solution containing 21.4 g of dimethyldisulphide in 100 ml of diethyl ether was added. The reaction mixture was warmed to room temperature and stirred for 30 minutes, was poured into water and the organic layer washed with water, with brine, and was then dried over magnesium sulphate and evaporated to dryness.

Workup

  1. temperatureThe mixture was warmed slowly over 10 minutes to 0° C.
  2. temperaturerefluxed for 1 hour
  3. additionwas added
  4. temperatureThe reaction mixture was warmed to room temperature
  5. washthe organic layer washed with water, with brine
  6. dry with materialwas then dried over magnesium sulphate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9e381083e85f47378f157bd737f1197c
Source dataset
uspto-grants-1988_04
Patent number
US04738959

Reaction notes

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