Hydrochloric Acid → Methyl 6-fluorochromane-4-carboxylate

HRID 487204Notes

Reaction equation

HRID 487204 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH:7]([C:11]([OH:13])=[O:12])[C:6]=2[CH:14]=1.Cl.[CH3:16]O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH:7]([C:11]([O:13][CH3:16])=[O:12])[C:6]=2[CH:14]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 139537996-Fluoro-3,4-dihydro-2H-1-benzopyran-4-carboxylic acid

Product 1

HCID 14986536Methyl 6-fluorochromane-4-carboxylate

Procedure

A solution of 8.4 g of the 6-fluoro-2,3-dihydro-4H-benzopyran-4-carboxylic acid in 580 mL of methanol was perfused with HCl gas for 5 minutes. The resulting solution was stirred at room temperature overnight. The volatiles were evaporated and the residue dissolved in ether. The ether layer was washed with water then dried over Na2SO4, filtered and evaporated to give 8.7 g of crude product which was purified by chromatography on 300 g of silica gel eluting with CH2Cl2 to give 6.2 g of product as an oil. NMR (CDCl3) ppm (delta): 2.00-2.40 (m, 2H), 3.80 (s, 3H), 2.5 (t, 1H, J=4 Hz), 7.10-6.70 (m, 3H).

Workup

  1. customThe volatiles were evaporated
  2. dissolutionthe residue dissolved in ether
  3. washThe ether layer was washed with water
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give 8.7 g of crude product which
  8. customwas purified by chromatography on 300 g of silica gel eluting with CH2Cl2

Sources & evidence

ORD record
ord-6359c97b87d6493d8935d9159bb10cc5
Source dataset
uspto-grants-1994_03
Patent number
US05294635

Reaction notes

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