Methanol → 6-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acid

HRID 1021371Notes

Reaction equation

HRID 1021371 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16]C)=[O:15])#[N:2].[OH-].[Na+].O.CO>C1COCC1.C(OCC)(=O)C.Cl>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[O:9][CH2:8][CH2:7][CH:6]2[C:14]([OH:16])=[O:15])#[N:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67080208Methyl 6-cyano-7-fluorochroman-4-carboxylate

Product 1

HCID 670802696-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acidYield 95.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylate (45 mg, 0.19 mmol) was diluted with THF (1 mL) followed the addition of NaOH (0.19 mL, 0.96 mmol), 200 μL of water and methanol. After stirring for 3 hours, the reaction was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield the title compound (40 mg, 95% yield).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-763ae18f72364dbb8c9faa6658c2c979
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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