Lithium Hydroxide → HCID 86621968, compound

HRID 2422505Notes

Reaction equation

HRID 2422505 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([O:20]C)=[O:19])=[CH:15][CH:16]=3)[O:11][C:10](=[O:22])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>C1COCC1.Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=3)[O:11][C:10](=[O:22])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86621969HCID 86621969, compound

Product 1

HCID 86621968HCID 86621968, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 4-(3-methylphenyl)-2-oxo-2H-chromene-7-carboxylate (610 mg, 2.1 mmol) in THF (21 mL) a solution of lithium hydroxide (10.3 mL, 10.3 mmol) was added. The solution was then heated at 65° C. for 2 hours. After cooling, volatiles were removed under reduced pressure and the residue obtained was diluted with THF (20 mL) and 2N HCl (40 mL). After 1 h stirring, the solid formed was collected by filtration to afford the title compound. 1H NMR (400 MHz, DMSO-d6): 13.5 (bs, 1H), 7.90 (d, 1H), 7.87 (dd, 1H), 7.59 (d, 1H), 7.48 (t, 1H), 7.43-7.33 (m, 3H), 6.55 (s, 1H), 2.41 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. customvolatiles were removed under reduced pressure
  3. customthe residue obtained
  4. customthe solid formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-85e15041d214485bb84b1597b592e937
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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