Ethanol → HCID 54185689, compound

HRID 1648098Notes

Reaction equation

HRID 1648098 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:24])[CH2:7][O:8][C:9]1[CH:22]=[C:21]2[C:12]([CH:13]=[CH:14][C:15]3[O:16][C:17](=[O:23])[CH2:18][CH2:19][C:20]=32)=[CH:11][CH:10]=1)(C)C.S(=O)(=O)(O)O.[CH2:30]([OH:32])[CH3:31]>>[CH2:30]([O:32][C:17](=[O:23])[CH2:18][CH2:19][C:20]1[C:21]2[C:12](=[CH:11][CH:10]=[C:9]([O:8][CH2:7][C:6]([O:5][CH2:2][CH3:1])=[O:24])[CH:22]=2)[CH:13]=[CH:14][C:15]=1[OH:16])[CH3:31]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 54352512HCID 54352512, compound

Product 1

HCID 54185689HCID 54185689, compoundYield 86%

Procedure

To a solution of 2.97 g (9.0 mmol) of [(2,3-dihydro-3-oxo-1H-naphtho[2,1-b]pyran-9-yl)oxy]acetic acid 1,1-dimethylethyl ester from the preceding example, in 120 mL of ethanol, was added 2 mL of concentrated sulfuric acid and the resulting solution was allowed to stir at room temperature for 13 days. Most of ethanol was removed under reduced pressure and the residue was dissolved in ether. The solution was washed with saturated aqueous sodium bicarbonate solution and work-up was completed in the usual manner. The crude product was purified by flash chromatography on 150 g silica gel, eluting with hexane-ethyl acetate (4:1). There was obtained 2.69 g (86.0%) of the title compound as a white solid, mp 112°-113° C.

Workup

  1. customMost of ethanol was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ether
  3. washThe solution was washed with saturated aqueous sodium bicarbonate solution and work-up
  4. customThe crude product was purified by flash chromatography on 150 g silica gel
  5. washeluting with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-b3f67ba8a6c4447f8705f1bf35cf9a01
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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