Diethyl Ether → HCID 11298655, compound

HRID 2261522Notes

Reaction equation

HRID 2261522 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=O)=O.[F-:20].[Cs+].C(O)(C)(C)C.C(OCC)C>CCCCCC.C(OCC)(=O)C>[F:20][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6386tert-ButanolHCID 25953Cesium fluorideHCID 11357963HCID 11357963, compound

Product 1

HCID 11298655HCID 11298655, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

280 mg (1.0 mmol) of 2-(3-methanesulfonyloxypropoxy)naphthalene and 456 mg (3.0 mmol) of cesium fluoride are added to a solvent of 4.0 mL of t-butanol. The reaction mixture is stirred for 6 hrs at 80° C. 7 mL of ethyl ether is added to the reaction mixture to remove metal salts. After filtration, the filtrate is concentrated by reduced pressure distiller. 188 mg (92% yield) of 2-(3-fluoropropoxy)naphthalene is obtained by column chromatography (ethyl acetate:n-hexane=1:20).

Workup

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

Sources & evidence

ORD record
ord-8262b4ceef6b4cafba49ff8811681d2f
Source dataset
uspto-grants-2010_12
Patent number
US07847092B2

Reaction notes

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