Acetic Acid → 7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acid

HRID 510717Notes

Reaction equation

HRID 510717 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5](C(O[Si](C)(C)C)(C#N)[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[C:19]([OH:22])(=[O:21])[CH3:20]>Cl.O.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:20]([C:19]([OH:22])=[O:21])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 670801887-Fluoro-4-(trimethylsilyloxy)chroman-4-carbonitrile

Product 1

HCID 670802337-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acidYield 83.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

7-Fluoro-4-(trimethylsilyloxy)chroman-4-carbonitrile (750 mg, 2.83 mmol) and SnCl2 dihydrate (2551 mg, 11.3 mmol) were diluted with glacial acetic acid (3 mL) and concentrated HCl (3 mL). The reaction was heated in an oil bath at 130° C. and stirred overnight. The reaction was allowed to cool, diluted with water and ethyl acetate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield the title compound (465 mg, 83.9% yield).

Workup

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

Sources & evidence

ORD record
ord-d46f88be40bf49f5a230a5c557d9cddc
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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