Carbon Dioxide → HCID 69956754, compound

HRID 2186509Notes

Reaction equation

HRID 2186509 reaction equation
[C:1](=[O:3])=[O:2].C1COCC1.[Li][C:10]1[S:20][C:13]2[C:14]3[CH:19]=[CH:18][S:17][C:15]=3[S:16][C:12]=2[CH:11]=1>O>[S:20]1[C:13]2[C:14]3[CH:19]=[CH:18][S:17][C:15]=3[S:16][C:12]=2[CH:11]=[C:10]1[C:1]([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 280Carbon Dioxide2×HCID 8028TetrahydrofuranHCID 178506649HCID 178506649, compound

Product 1

HCID 69956754HCID 69956754, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

Carbon dioxide was added in small lumps to a flask against a fast flow of nitrogen. The flask was then sealed under a nitrogen bubbler and cooled to the −78° C. THF was added to cover the CO2 and the mixture stirred. The cooled lithiodithienothiophene was added dropwise via syringe and a violent reaction was observed resulting in the formation of a yellow suspension. Once addition was complete the mixture was allowed to warm to r.t. during which time the mixture turned to an off white colour. After stirring for a further 30 min. water (30 cm3) was added and the mixture turned to a light green/brown solution. This was washed with ether (2×20 cm3) and the organics discarded. The aqueous layer was acidified by the addition of HCl (10 cm3, 5 M) which precipitated out a fine yellow solid. Recrystallisation was attempted in 33% acetic acid. A fine, insoluble suspension remained after heating and this was left to further crystallise overnight to give the title compound as a fine yellow/green powder (286 mg, 61%); δH 7.31, (1H, d, J5.1), 7.56 (2H, d, J5.1), 7.94 (1H, s); v max/cm−1 (KBr) 3090 m, 2823 m, 2559 m, 1652 s, 1504 s, 1470 w, 1428 s, 1311 s, 1265 m, 1164 m, 928 s, 750 s, 716 s and 602 s; m.p. 276° C. (sublimes) m.p.(lit.reference 29) 275-277° C.)

Workup

  1. customThe flask was then sealed under a nitrogen bubbler
  2. customa violent reaction
  3. customwas observed resulting in the formation of a yellow suspension
  4. additionOnce addition
  5. temperatureto warm to r.t. during which time the mixture
  6. additionwas added
  7. washThis was washed with ether (2×20 cm3)
  8. additionThe aqueous layer was acidified by the addition of HCl (10 cm3, 5 M) which
  9. customprecipitated out a fine yellow solid
  10. customRecrystallisation
  11. temperatureafter heating
  12. waitthis was left
  13. customto further crystallise overnight

Sources & evidence

ORD record
ord-72e0b95fb65d450a850a4cf163fff430
Source dataset
uspto-grants-2002_06
Patent number
US06403809B1

Reaction notes

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