Carbon Dioxide → HCID 10824737, compound

HRID 2384900Notes

Reaction equation

HRID 2384900 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH3:13])[CH:12]=2)=[CH:4][CH:3]=1.[Li]C(C)(C)C.[C:19](=[O:21])=[O:20]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:19]([OH:21])=[O:20])=[C:11]([CH3:13])[CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 68952924HCID 68952924, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 10824737HCID 10824737, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve 2-(4-chloro-phenyl)-4-methyl-thiophene (0.53 g, 1.85 mmol) in THF (25 mL) and cool to −78° C. Add t-BuLi (1.7 M, 2.3 mL, 3.88 mmol) dropwise. Stir the solution at −78° C. for 20 min. Cannulate the solution into a flask containing powdered dry ice (10 g). Stir the reaction and allow to warm to RT. Quench the reaction with saturated NH4Cl (10 mL), dilute with water (40 mL), and extract with EtOAc (2×50 mL). Dry the combined organic layers over Na2SO4, filter, and concentrate. Purify the crude material by washing with hexane (2×20 mL) to give 0.35 g (74%) of the title compound. LC-MS/ES m/z (35Cl) 251.0 [M−H]−.

Workup

  1. stirringStir
  2. customthe reaction
  3. temperatureto warm to RT
  4. customQuench
  5. customthe reaction with saturated NH4Cl (10 mL)
  6. extractionextract with EtOAc (2×50 mL)
  7. dry with materialDry the combined organic layers over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify the crude material
  11. washby washing with hexane (2×20 mL)

Sources & evidence

ORD record
ord-ddf293d19cfc43f6a3b0d5fb03254703
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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