Water → 2-Benzyloxy-5-trifluoromethyl-benzylazide

HRID 392910Notes

Reaction equation

HRID 392910 reaction equation
C1CCN2C(=NCCC2)CC1.C1(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:29]([O:36][C:37]1[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][C:38]=1[CH2:39]O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>C1(C)C=CC=CC=1>[CH2:29]([O:36][C:37]1[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][C:38]=1[CH2:39][N:26]=[N+:27]=[N-:28])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 179473082-Benzyloxy-5-trifluoromethyl-benzylalcohol

Product 1

HCID 226619412-Benzyloxy-5-trifluoromethyl-benzylazideYield 84.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

DBU (1 mL, 6.62 mmol) and diphenyl phosphoryl azide (1.6 mL, 7.5 mmol) were added to a solution of 2-benzyloxy-5-trifluoromethyl-benzyl alcohol (1.24 g, 4.41 mmol) in anhydrous toluene (10 mL) at room temperature. After 3 hours, water was added and the mixture extracted with ethyl acetate (3×). The combined organic layers were washed with 1N HCl (1×), brine (1×), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (3% ethyl acetate/hexanes) to afford 1.14 grams of the title compound as a colorless oil (84%). MS 280 (M−N2)+. 1H NMR (400 MHz, CDCl3) δ 7.6-7.3 (m, 7H); 7.01 (d, 1H, J=9.1 Hz); 5.18 (s, 2H); 4.42 (s, 2H).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with 1N HCl (1×), brine (1×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (3% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-fb880838aaf542c8b4ac0d3ef16a911f
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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