Water → HCID 23123945, compound

HRID 350845Notes

Reaction equation

HRID 350845 reaction equation
[CH2:1]1[CH2:17][O:16][C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([CH2:4][CH2:5][CH2:6][N:7]=[N+]=[N-])[O:2]1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:17]1[CH2:1][O:2][C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([CH2:4][CH2:5][CH2:6][NH2:7])[O:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 231239164,4-Ethylenedioxy-4-phenylbutylazide

Product 1

HCID 23123945HCID 23123945, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4,4-Ethylenedioxy-4-phenylbutylazide (130.0 mg, 0.56 mmol) was dissolved in tetrahydrofuran (5 ml), and thereto were added water (0.01 ml, 0.56 mmol) and triphenylphosphine (146.2 mg, 0.56 mmol) in a tetrahydrofuran solution (2 ml) in sequential order at the same temperature, and thereafter, the solution was stirred at room temperature for 24 hours. The reaction solution was added to a saturated aqueous sodium hydrogencarbonate solution and then extracted by chloroform, to obtain an organic layer. The extracted organic was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant substance was purified by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound was obtained as a colorless oil (61.8 mg, 56.4% for 2 steps).

Workup

  1. extractionextracted by chloroform
  2. customto obtain an organic layer
  3. washThe extracted organic was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant substance was purified by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound
  7. customwas obtained as a colorless oil (61.8 mg, 56.4% for 2 steps)

Sources & evidence

ORD record
ord-714385c1810d4cc9bf9d7a9582723540
Source dataset
uspto-grants-2007_02
Patent number
US07183295B2

Reaction notes

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