Water → HCID 22672162, compound

HRID 1006565Notes

Reaction equation

HRID 1006565 reaction equation
[N:1]([CH2:4][C:5]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:6]=1[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:6]=1[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 22672055HCID 22672055, compound

Product 1

HCID 22672162HCID 22672162, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(2-azidomethyl-5-chlorophenoxymethyl)-benzoate (389 mg; prepared in Reference Example 49) in THF (4.0 ml), triphenylphosphine (462 mg) was added at room temperature. The mixture was stirred for 3 hours. After stirring, water was added thereto. The mixture was stirred for 15 hours. The reaction mixture was concentrated under the reduced pressure. the residue was purified on silica gel column chromatography (CHCL3:MeOH=50:1→10:1) to give the title compound (339 mg) having the following physical data.

Workup

  1. stirringAfter stirring
  2. stirringThe mixture was stirred for 15 hours
  3. concentrationThe reaction mixture was concentrated under the reduced pressure
  4. customthe residue was purified on silica gel column chromatography (CHCL3:MeOH=50:1→10:1)

Sources & evidence

ORD record
ord-690265216e5e4ea28f05eafa7580249f
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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