Potassium Hydroxide → HCID 13102419, compound

HRID 1446382Notes

Reaction equation

HRID 1446382 reaction equation
[CH3:1][C:2]1([C:11]([O:13]C)=[O:12])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[O:3]1.[OH-].[K+]>CS(C)=O.O>[CH3:1][C:2]1([C:11]([OH:13])=[O:12])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68674503HCID 68674503, compound

Product 1

HCID 13102419HCID 13102419, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-methyl-2,3-dihydrobenzofuran-2-carboxylate (Step B, 0.22 g, 1.1 mmol) in 5 mL of dimethylsulfoxide was added potassium hydroxide (0.64 g, 11 mmol) in 0.5 mL of water. After stirring at room temperature for 1 h, the reaction mixture was partitioned between ether (50 mL) and 1 M hydrochloric acid (50 mL). The organic layer was separated and the aqueous layer extracted with ether (3×50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.17 (d, 1H), 7.12 (t, 1H), 6.86 (t, 1H), 6.79 (d, 1H), 3.60 (d, 1H), 3.18 (d, 1H), 1.67 (s, 3H).

Workup

  1. customthe reaction mixture was partitioned between ether (50 mL) and 1 M hydrochloric acid (50 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with ether (3×50 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f41a12b970db4ae798a136e92ebfdefe
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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