Diethyl Ether → HCID 11298655, compound

HRID 2261523Notes

Reaction equation

HRID 2261523 reaction equation
C1(C)C(S(O[CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)(=O)=O)=CC=CC=1.[F-:26].[Cs+].C(O)(CC)(C)C.C(OCC)C>CCCCCC.C(OCC)(=O)C>[F:26][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 64052-Methyl-2-butanolHCID 25953Cesium fluorideHCID 86621610HCID 86621610, compound

Product 1

HCID 11298655HCID 11298655, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

356 mg (1.0 mmol) of 2-(3-toluenesulfonyloxypropoxy)naphthalene and 456 mg (3.0 mmol) of cesium fluoride are added to 4.0 mL of t-amyl alcohol in a reaction vessel. The reaction mixture is stirred for 2 hrs at 90° C. 7 mL of ethyl ether is added to remove metal salt. After filtration, the filtrate is concentrated by a reduced pressure distiller. 190 mg (93% yield) of 2-(3-fluoropropoxy)naphthalene is obtained by column chromatography (ethyl acetate:n-hexane=1:20).

Workup

  1. customto remove metal salt
  2. filtrationAfter filtration
  3. concentrationthe filtrate is concentrated by a reduced pressure distiller

Sources & evidence

ORD record
ord-34f767da45f24f22988fbbd272417582
Source dataset
uspto-grants-2010_12
Patent number
US07847092B2

Reaction notes

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