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

HRID 1626379Notes

Reaction equation

HRID 1626379 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. overnight. The reaction was cooled, then diluted with water and ethyl acetate. The layers were separated and the organic layer was dried over magnesium sulfate, filtered and concentrated to yield the title compound (465 mg, 83.9% yield).

Workup

  1. temperatureThe reaction was cooled
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8703ae897e8c40cebe5d31fa94c290d6
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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