Carbon Dioxide → 4-Isobutoxy-benzo[b]thiophene-2-carboxylic acid

HRID 1929237Notes

Reaction equation

HRID 1929237 reaction equation
C([Li])CCC.CCCCCC.[CH2:12]([O:16][C:17]1[C:25]2[CH:24]=[CH:23][S:22][C:21]=2[CH:20]=[CH:19][CH:18]=1)[CH:13]([CH3:15])[CH3:14].[C:26](=[O:28])=[O:27]>C(OCC)C>[CH2:12]([O:16][C:17]1[C:25]2[CH:24]=[C:23]([C:26]([OH:28])=[O:27])[S:22][C:21]=2[CH:20]=[CH:19][CH:18]=1)[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 280Carbon Dioxide2×HCID 8058HexaneHCID 596002244-Isobutoxy-benzo[b]thiopheneHCID 178418339Butyllithium

Product 1

HCID 596002594-Isobutoxy-benzo[b]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A 1.6 M solution of n-butyl lithium in hexane (18 ml, 28.8 mmol) is dissolved under an argon atmosphere in 100 ml of dry diethyl ether, followed by dropwise addition of a solution of 4-Isobutoxy-benzo[b]thiophene (201, 5.4 g, 26.1 mmol) in 40 ml of diethyl ether. The reaction mixture is refluxed for 45 min, then cooled down and transferred via syringe to a mixture of excess dry ice (115 g, 2.61 mol) in diethyl ether (the dry ice is washed before twice with diethyl ether). The mixture is allowed to stir overnight at room temperature, then distributed between diethyl ether and water. The ether layers are reextracted with water. The aqueous layers are acidified with 2M aqueous HCl solution, and the precipitate is filtered off, washed with water and dried under high vacuum.

Workup

  1. temperatureThe reaction mixture is refluxed for 45 min
  2. temperaturecooled down
  3. washis washed before twice with diethyl ether)
  4. filtrationthe precipitate is filtered off
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-704cf05ff4f24bd89e2b1e970932aaa1
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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