Sodium Hydroxide → 6-fluoro-3,4-dihydro-4-(hydroxymethyl)-2H-benzopyran-4-carboxylic acid

HRID 487206Notes

Reaction equation

HRID 487206 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][C:7]([CH2:15][OH:16])([C:11]([O:13]C)=[O:12])[C:6]=2[CH:17]=1.[OH-].[Na+]>C(Cl)Cl.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][C:7]([CH2:15][OH:16])([C:11]([OH:13])=[O:12])[C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14986537Methyl 6-fluoro-3,4-dihydro-4-(hydroxymethyl)-2H-benzopyran-4-carboxylate

Product 1

HCID 149865386-fluoro-3,4-dihydro-4-(hydroxymethyl)-2H-benzopyran-4-carboxylic acidYield 41.2%

Reagents, catalysts & solvents 1

HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

To a solution of 7 g (0.029 mole) Methyl 6-fluoro-3,4-dihydro-4-(hydroxymethyl)-2H-benzopyran-4-carboxylate in 200 mL of McOH was added 7.2 mL of 5N NaOH. The reaction was heated on a steam bath overnight then cooled to room temperature. The MeOH was evaporated and the residue dissolved in water then acidified to pH 4.0 with concentrated HCl. The aqueous was extracted with EtOAc and the EtOAc layer was dried over Na2SO4, filtered and evaporated to give 6 g of crude product. Chromatography on 160 g of silica gel eluting with CH2Cl2 /ether gave 2.7 g of product, m.p. 134°-135° C.

Workup

  1. temperatureThe reaction was heated on a steam bath overnight
  2. customThe MeOH was evaporated
  3. dissolutionthe residue dissolved in water
  4. extractionThe aqueous was extracted with EtOAc
  5. dry with materialthe EtOAc layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give 6 g of crude product

Sources & evidence

ORD record
ord-c2640519d4c043c9ac313089dcf00d0c
Source dataset
uspto-grants-1994_03
Patent number
US05294635

Reaction notes

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