Carbon Dioxide → HCID 22388390, compound

HRID 1699855Notes

Reaction equation

HRID 1699855 reaction equation
[Mg].Br[C:3]1[C:8]2[S:9][CH:10]=[C:11]([CH2:12][CH3:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1.CI.[C:16](=[O:18])=[O:17].Cl>CCOCC>[C:16]([C:3]1[C:8]2[S:9][CH:10]=[C:11]([CH2:12][CH3:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1)([OH:18])=[O:17]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 22388507HCID 22388507, compound

Product 1

HCID 22388390HCID 22388390, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Magnesium (2.67 g) was stirred in ether (15 ml) at room temperature. A solution of 7-bromo-3-ethylbenzo[b]thiophene (4.40 g) and methyl iodide (7.76 g) in ether (50 ml) were added dropwise over 30 min. Then, refluxing was conducted for 50 min and the reaction mixture was cooled in ice water bath. Using a separate reaction vessel, pulverized dry ice was stirred in ether, and the Grignard reagent prepared above was transferred to the vessel for about 5 min. To the reaction mixture was added 2N hydrochloric acid to acidify the solution, and the ether layer was separated. The solution was made alkaline with a 5% aqueous sodium hydroxide solution. 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 (3.22 g) as crystals.

Workup

  1. temperatureThen, refluxing
  2. customa separate reaction vessel
  3. waitwas transferred to the vessel for about 5 min
  4. customthe ether layer was separated
  5. extractionAfter extraction with ether
  6. dry with materialthe extract was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-17559ded019b4269829475b7508fbcff
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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