Triphenylphosphine → 5,6-Dihydroimidazo[1,5-d][1,4]benzoxazepine

HRID 404255Notes

Reaction equation

HRID 404255 reaction equation
O[CH2:2][CH2:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:7][N:6]=[CH:5]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:7]1[N:6]=[CH:5][N:4]2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:2][CH2:3]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 582941365-(2-Hydroxyphenyl)-1H-imidazole-1-ethanol

Product 1

HCID 582941105,6-Dihydroimidazo[1,5-d][1,4]benzoxazepineYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(1-(2-hydroxyethyl)-1H-imidazol-5-yl)phenol (103.0 mg, 0.5 mmol) and PPh3 (157.0 mg, 0.6 mmol) in THF (4 mL) at 0° C., was added DEAD (0.22 mL, 40% solution in toluene, 0.75 mmol). The resulting yellow solution was allowed to warm to rt and stirred overnight. The solvent was removed under reduced pressure and the crude residue was purified by flash column chromatography on silica gel to afford the desired product in 84% yield. 1H NMR: 4.35-4.45 (m, 4H), 6.94-7.05 (m, 2H), 7.11-7.19 (m, 1H), 7.43 (d, 1H, J=0.8 Hz), 7.49 (s, 1H), 7.67 (dd, 1H, J=1.6, 8.0 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b5afb2c1b9e847f791564d107c9f3382
Source dataset
uspto-grants-2014_06
Patent number
US08748469B2

Reaction notes

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