Water → HCID 178493746, compound

HRID 2236535Notes

Reaction equation

HRID 2236535 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[C:8]([O:12][CH3:13])=[CH:7][N:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[C:8]([O:12][CH3:13])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 178493750HCID 178493750, compound

Product 1

HCID 178493746HCID 178493746, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-azidomethyl-5-methoxy-pyridin-4-ol (1.45 g, 8.05 mole), is then suspended in 20 mL of tetrahydrofuran and treated with triphenylphosphine (2.11 g, 8.05 mmole) after stirring for 10 mins at ambient temperature water is added (1.76 mL, 15 equivalents) and the reaction mixture is stirred at ambient temperature overnight. The solids gradually dissolved followed by the formation of a precipitate. The resulting solid is filtered, washed with fresh 10:1 tetrahydrofuran:water and dried to give, 0.897 g, (88%), mp 196-201° C. dec; MS (ES+): m/z 155.3 (M+H).

Workup

  1. additionis added (1.76 mL, 15 equivalents)
  2. dissolutionThe solids gradually dissolved
  3. filtrationThe resulting solid is filtered
  4. washwashed with fresh 10:1 tetrahydrofuran
  5. dry with materialwater and dried
  6. customto give

Sources & evidence

ORD record
ord-7d060fb69dad4ac4b5e961131c310b3e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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