5-Phenylisoxazole-3-carboxaldehyde → (5-Phenylisoxazol-3-yl)(3,4,5-trimethoxyphenyl)methanol

HRID 63196Notes

Reaction equation

HRID 63196 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH:12]=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23]>C1COCC1>[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH:12]([C:18]3[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:16]([O:15][CH3:14])[CH:17]=3)[OH:13])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 71723055-Phenylisoxazole-3-carboxaldehydeHCID 178492974HCID 178492974, compound

Product 1

HCID 53364193(5-Phenylisoxazol-3-yl)(3,4,5-trimethoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-phenylisoxazole-3-carbaldehyde 38i (0.365 g, 2.1 mmol) in 15 mL THF was added a THF solution of 3,4,5-trimethoxyphenylmagnesiumbromide (0.5 N, 5.5 mL, 2.74 mmol) at 0° C. The mixture was allowed to stir for 30 min and quenched with satd. NH4Cl, extracted with ethyl ether, dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 40i as a white solid. (48.8%). 1H NMR (CDCl3) δ 7.78-7.77 (m, 2H), 7.48-7.46 (m, 3H), 6.74 (s, 2H), 6.45 (s, 1H), 5.98 (d, 1H, J=3.5 Hz) 3.89 (s, 6H), 3.86 (s, 3H), 2.77 (d, 1H, J=3.5 Hz); MS (ESI) m/z 364.1 (M+Na)+.

Workup

  1. customquenched with satd
  2. extractionNH4Cl, extracted with ethyl ether
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e213deb7074249329b78c2fa02317aeb
Source dataset
uspto-grants-2016_09
Patent number
US09447049B2

Reaction notes

Loading…