Water → HCID 178465141, compound

HRID 2368135Notes

Reaction equation

HRID 2368135 reaction equation
[N:1]([CH:4]([CH3:27])[CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[O:14][C:15]3[CH:21]=[C:20]([O:22][CH2:23][CH:24]4[CH2:26][CH2:25]4)[CH:19]=[CH:18][C:16]=3[CH:17]=2)[CH2:9][CH2:8]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH:24]1([CH2:23][O:22][C:20]2[CH:19]=[CH:18][C:16]3[CH:17]=[C:13]([C@H:10]4[CH2:11][CH2:12][C@H:7]([O:6][CH2:5][CH:4]([NH2:1])[CH3:27])[CH2:8][CH2:9]4)[O:14][C:15]=3[CH:21]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 178459231HCID 178459231, compound

Product 1

HCID 178465141HCID 178465141, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[trans-4-(2-azidopropoxy)cyclohexyl]-6-(cyclopropylmethoxy)-1-benzofuran (397 mg) and triphenylphosphine (564 mg) in THF (4 mL)/water (2 mL) was stirred at 60° C. overnight. The reaction mixture was allowed to cool to room temperature, and extracted with ethyl acetate and water. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (ethyl acetate/methanol) to give the title compound (373 mg).

Workup

  1. extractionextracted with ethyl acetate and water
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-a36853539a3a4d31b82959144f56e021
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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