Benzaldehyde, 4-(phenylmethoxy)- → (4-(Benzyloxy)phenyl)(3-methyl-3H-1,2,3-triazol-4-yl)methanol

HRID 731190Notes

Reaction equation

[Li]CCCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[N:8]1.[CH2:12]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCCCCC.C1COCC1>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([CH:24]([C:11]2[N:7]([CH3:6])[N:8]=[N:9][CH:10]=2)[OH:25])=[CH:26][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of n-BuLi (11.6 mL, 1.6 M, 18.6 mmol) in hexane was added dropwise to a solution of 73.1 (1.29 g, 15.5 mmol) in THF (75 mL) at −40° C. After stirring at −40° C. for 2 hours, 4-(benzyloxy)benzaldehyde was added at −40° C., and the reaction was warmed to room temperature. The reaction was quenched saturated NH4Cl (aq) after 3 hours of stirring and then extracted with EtOAc. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue 73.2 was used in the next reaction without further purification. MS ESI (pos.) m/e 296.2 (M+H).

Workup

temperaturethe reaction was warmed to room temperature
customThe reaction was quenched saturated NH4Cl (aq) after 3 hours
stirringof stirring
extractionextracted with EtOAc
washThe organic phase was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue 73.2 was used in the next reaction without further purification

Sources & evidence

ORD record: ord-2f546afd0078408e90e13d7c0b338e69
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582803B2

Reaction notes

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