Carbon Dioxide → Anofinic acid

HRID 1489187Notes

Reaction equation

HRID 1489187 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]([CH3:11])([CH3:10])[CH:8]=[CH:9][C:4]=2[CH:3]=1.C([Li])CCC.[C:19](=[O:21])=[O:20]>O1CCCC1.CCCCCC>[CH3:10][C:7]1([CH3:11])[O:6][C:5]2[CH:12]=[CH:13][C:2]([C:19]([OH:21])=[O:20])=[CH:3][C:4]=2[CH:9]=[CH:8]1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 117705336-Bromo-2,2-dimethyl-2H-chromeneHCID 178418339Butyllithium

Product 1

HCID 5319235Anofinic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 6-bromo-2,2-dimethyl-2H-benzo[b]pyran (see J. Med. Chem., 33, 3028 [1990]) (5.0 g) in dry tetrahydrofuran (100 ml) at -70° C. under nitrogen was added, dropwise, a 1.6M solution of n-butyllithium in hexane (17 ml). The reaction mixture was stirred at -70° C. for 15 minutes then treated with an excess of finely ground solid CO2. The reaction was further stirred for one hour, the solvent evaporated in vacuo and the residue taken up in ethyl acetate and washed with dilute aqueous hydrochloric acid. The organic layer was concentrated in vacuo to a solid which was triturated with hexane to provide a white solid, 1.6 g.

Workup

  1. stirringThe reaction was further stirred for one hour
  2. customthe solvent evaporated in vacuo
  3. washwashed with dilute aqueous hydrochloric acid
  4. concentrationThe organic layer was concentrated in vacuo to a solid which
  5. customwas triturated with hexane
  6. customto provide a white solid, 1.6 g

Sources & evidence

ORD record
ord-669eeea9fe1149999c7e234a01a87f5a
Source dataset
uspto-grants-1997_10
Patent number
US05677324

Reaction notes

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