Carbon Dioxide → HCID 22388445, compound

HRID 1072824Notes

Reaction equation

HRID 1072824 reaction equation
[Mg].Br[C:3]1[CH:13]=[CH:12][C:6]2[O:7][C:8]([CH2:10][CH3:11])=[CH:9][C:5]=2[CH:4]=1.CI.[C:16](=[O:18])=[O:17].Cl>CCOCC>[C:16]([C:3]1[CH:13]=[CH:12][C:6]2[O:7][C:8]([CH2:10][CH3:11])=[CH:9][C:5]=2[CH:4]=1)([OH:18])=[O:17]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 122474825-BROMO-2-ETHYLBENZOFURAN

Product 1

HCID 22388445HCID 22388445, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Magnesium (1.50 g) was stirred in ether (30 ml) at room temperature. Thereto was dropwise added a solution of 5-bromo-2-ethylbenzo[b]furan (8.30 g) and methyl iodide (0.55 g) in ether (30 ml) over 30 min. Then, the mixture was refluxed for 50 min and cooled in an ice water bath. In a different container, pulverized dry ice was stirred in ether and the Grignard reagent prepared above was transferred over about 5 min. 2N Hydrochloric acid was added to the reaction mixture to acidify the solution, and the ether layer was separated. The solution was basified with a 5% aqueous solution of sodium hydroxide and the separated aqueous layer was acidified with 2N hydrochloric acid. After extraction with ether, the extract was dried over sodium sulfate and concentrated to give the objective compound (2.48 g).

Workup

  1. temperatureThen, the mixture was refluxed for 50 min
  2. temperaturecooled in an ice water bath
  3. customthe ether layer was separated
  4. extractionAfter extraction with ether
  5. dry with materialthe extract was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d8e20564699341b4853c24d939017ae9
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

Loading…