1-Methyl-3-phenyl-1H-1,2,4-triazole-5-carbaldehyde → (3,3-dimethyl-1,3-dihydroisobenzofuran-5-yl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

HRID 2105068Notes

Reaction equation

[Li]CCCC.Br[C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][O:12][C:13]2([CH3:17])[CH3:16])=[CH:9][CH:8]=1.[CH3:18][N:19]1[C:23]([CH:24]=[O:25])=[N:22][C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:20]1>C1COCC1>[CH3:16][C:13]1([CH3:17])[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([CH:24]([C:23]3[N:19]([CH3:18])[N:20]=[C:21]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:22]=3)[OH:25])[CH:15]=2)[CH2:11][O:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

BuLi (0.36 mL, 1.6 M in hexanes, 0.57 mmol) was added dropwise to a solution of Intermediate 388.2 (110 mg, 0.49 mmol) in THF (5 mL) at −78° C. After stirring 5 min, a solution of Intermediate 386.1 (100 mg, 0.54 mmol) in THF (3 mL) was added. The mixture was warmed to 0° C. over 2 h and quenched with sat. NH4Cl (1 mL). The mixture was diluted with H2O (20 mL) and extracted with EtOAc (3×20 mL). The organics were combined, washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (hexanes, EtOAc) yielded 63 mg of Intermediate 388.3 as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 6 H) 3.48 (s, 3H) 4.90 (s, 2H) 5.68 (s, 1H) 6.01 (s, 1H) 6.93-7.00 (m, 1H) 7.10-7.14 (m, 1H) 7.14-7.19 (m, 1H) 7.28-7.38 (m, 3H) 7.89-7.95 (m, 2H)

Workup

customquenched with sat. NH4Cl (1 mL)
additionThe mixture was diluted with H2O (20 mL)
extractionextracted with EtOAc (3×20 mL)
washwashed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customPurification by flash chromatography (hexanes, EtOAc)

Sources & evidence

ORD record: ord-22242ae04ba54e6fb11998eacfc13c87
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576098B2

Reaction notes

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