Dimethylformamide → 4-Azido-2-fluorocyclohexyl 2-phenylethyl ether

HRID 271381Notes

Reaction equation

HRID 271381 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CN(C)C=O.CS(O[CH:15]1[CH2:20][CH2:19][CH:18]([O:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]([F:30])[CH2:16]1)(=O)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CCCCCC>[C:24]1([CH2:23][CH2:22][O:21][CH:18]2[CH2:19][CH2:20][CH:15]([N:1]=[N+:2]=[N-:3])[CH2:16][CH:17]2[F:30])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 725741513-Fluoro-4-(2-phenylethoxy)cyclohexyl methanesulfonate

Product 1

HCID 725741444-Azido-2-fluorocyclohexyl 2-phenylethyl etherYield 71.3%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Sodium azide (0.500 g, 7.69 mmol) was added to a N,N-dimethylformamide (10 mL) solution of 3-Fluoro-4-(2-phenylethoxy)cyclohexyl methanesulfonate (0.597 g, 1.89 mmol) under nitrogen. The resulting mixture was heated at 50° C. for 24 h, then cooled and poured into saturated sodium bicarbonate. The aqueous mixture was extracted with ethyl acetate (3×) and the combined organic extracts were washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Flash column chromatography (hexane:ethyl acetate, e 90:10) gave 4-Azido-2-fluorocyclohexyl 2-phenylethyl ether as a colorless oil (0.355 g, 71% yield).

Workup

  1. temperaturecooled
  2. extractionThe aqueous mixture was extracted with ethyl acetate (3×)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81fe9cfaea934dff9d015e01ebe48919
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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