Tetrahydrofuran → methyl 7-fluoro-3,4-dihydro-2H-chromene-4-carboxylate

HRID 1626380Notes

Reaction equation

HRID 1626380 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[CH2:15]1COCC1>CO.S(=O)(=O)(O)O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 8028TetrahydrofuranHCID 670802337-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acid

Product 1

HCID 67080260methyl 7-fluoro-3,4-dihydro-2H-chromene-4-carboxylateYield 98.7%

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
55 °C

Procedure

7-Fluoro-3,4-dihydro-2H-chromene-4-carboxylic acid (346 mg, 1.76 mmol) was diluted with THF (2 mL), methanol (2 mL) and 4 drops of sulfuric acid. The reaction was heated at 55° C. and stirred for 12 hours. The reaction was cooled to ambient temperature, diluted with ethyl acetate and saturated sodium bicarbonate. The layers were separated and the organic layer was dried over magnesium sulfate, filtered and concentrated to yield the title compound (366 mg, 98.7% yield).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  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-96ac8ebb6051416bb791564e1c7d51c5
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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