Hydrochloric Acid → HCID 53674838, compound

HRID 1414655Notes

Reaction equation

HRID 1414655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9](O)[CH:8]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:6]2.C(N(CC)C(F)(F)C([F:25])Cl)C.C(Cl)Cl.Cl>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([F:25])[CH:8]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:6]2.[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:14][C:15]([O-:17])=[O:16])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 1361842-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amineHCID 21408131HCID 21408131, compound

Product 2

HCID 53674838HCID 53674838, compoundHCID 86733917HCID 86733917, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 g. of methyl 6-methoxy-1-hydroxy-1,2,3,4-tetrahydro-2-naphthylacetate, 38 g. of 1-diethylamino-1,1,2-trifluoro-2-chloroethane and 150 ml. of methylene chloride are allowed to stand for 24 hours. The fluorination reaction mixture is added to 250 ml. of water containing 12 g. of hydrogen chloride; the resulting mixture is separated and the methylene chloride phase is washed with water, dried over sodium sulfate, and evaporated to yield methyl 6-methoxy-1-fluoro-1,2,3,4-tetrahydro-2-naphthylacetate and 6-methoxy-1,2-dihydro-2-naphthylacetate. The mixture is separated on alumina eluting with acetone: diethyl ether (1:4) and the separated fractions are identified by ultraviolet spectroscopy. The fraction containing methyl 6-methoxy-1-fluoro-2-naphthylacetate is evaporated and the residue is refluxed with 23 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 500 ml. of xylene for six hours. The cooled mixture is filtered and chromatographed on alumina eluting with chloroform. The fraction containing the product is evaporated to yield methyl 6-methoxy-1-fluoro-2-naphthylacetate.

Workup

  1. additionA mixture of 25 g
  2. customThe fluorination reaction mixture
  3. additionis added to 250 ml
  4. customthe resulting mixture is separated
  5. washthe methylene chloride phase is washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-4c665b8b96204ecfb9050a5808422379
Source dataset
uspto-grants-1977_01
Patent number
US04001301

Reaction notes

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