Carbon Dioxide → HCID 11287530, compound

HRID 413016Notes

Reaction equation

HRID 413016 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[C:9]([CH:15]=[CH2:16])[C:8]=1[O:17][CH3:18].[C:19](=[O:21])=[O:20].[OH-].[Na+]>C1COCC1.CCOC(C)=O>[CH3:18][O:17][C:8]1[C:9]([CH:15]=[CH2:16])=[C:10]([S:13][CH3:14])[CH:11]=[CH:12][C:7]=1[C:19]([OH:21])=[O:20]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 11436844HCID 11436844, compoundHCID 178418339Butyllithium

Product 1

HCID 11287530HCID 11287530, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-100 °C

Procedure

At −100° C., n-BuLi (25 ml, 15% in n-hexane, 4.1 mmol) was added to a solution of 1-bromo-2-methoxy-4-methylsulfanyl-3-vinylbenzene (7 g, 31.3 mmol) in THF (300 ml), and the mixture was stirred at −100° C. for 20 min. At −100° C., CO2 was then introduced (exothermic reaction up to −60° C.). At −80 to −90° C., the mixture was then stirred for another 1 h, and NaOH (100 ml) was added dropwise at −40° C. The solution was stirred into EtOAc (400 ml), and the mixture was extracted 3× with 5% strength NaOH and acidified to pH=1 using 10% strength HCl. The H2O phase was extracted with EtOAc (300 ml), and the combined organic phases were dried over MgSO4 and concentrated.

Workup

  1. custom(exothermic reaction up to −60° C.)
  2. stirringAt −80 to −90° C., the mixture was then stirred for another 1 h
  3. extractionthe mixture was extracted 3× with 5% strength NaOH
  4. extractionThe H2O phase was extracted with EtOAc (300 ml)
  5. dry with materialthe combined organic phases were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9d759e6164542fc9dd623064492e057
Source dataset
uspto-grants-2003_05
Patent number
US06566307B1

Reaction notes

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