Hydrochloric Acid → Methyl 6-fluoro-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylate

HRID 326290Notes

Reaction equation

HRID 326290 reaction equation
[H-].[Na+].CO[C:5](=[O:8])[O:6][CH3:7].[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[CH2:15][CH2:14][CH2:13]2.Cl>O1CCCC1.CCOCC.CCCCCC>[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[CH:15]([C:5]([O:6][CH3:7])=[O:8])[CH2:14][CH2:13]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 149151166-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 19927550Methyl 6-fluoro-1,2,3,4-tetrahydro-1-oxo-2-naphthalenecarboxylateYield 98.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Hexane washed sodium hydride (3.5 g of 60%, 88 mmole) was covered with 75 ml of tetrahydrofuran and 5.4 ml (64 mmole) of dimethylcarbonate was added in one portion. The solution was heated to reflux and 6-fluoro-3,4-dihydro-1(2H)-naphthlenone (7.2 g, 44 mmole) in 25 ml of tetrahydrofuran was added dropwise while maintaining reflux. After the addition was complete, the reaction was refluxed for 1.5 hours. The reaction was then cooled in an ice bath and 10% aqueous HCl solution was carefully added. The solution was diluted with ether and the aqueous phase was separated and extracted twice with ether. The combined organic phases were dried (MgSO4) and concentrated. The crude product was a pale yellow solid (9.6 g, 98% yield).

Workup

  1. additionwas added in one portion
  2. temperatureThe solution was heated
  3. temperatureto reflux
  4. temperaturewhile maintaining
  5. temperaturereflux
  6. additionAfter the addition
  7. temperaturethe reaction was refluxed for 1.5 hours
  8. temperatureThe reaction was then cooled in an ice bath
  9. customthe aqueous phase was separated
  10. extractionextracted twice with ether
  11. dry with materialThe combined organic phases were dried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-0c5802f496d94262be346f01a287f95a
Source dataset
uspto-grants-1993_12
Patent number
US05268388

Reaction notes

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