(1-Isopropyl-2-methyl-propyl)-(2,4,5-trimethoxy-benzylidene)-amine → (2-Isopropyl4,5-dimethoxy-benzylidene)-(1-isopropyl-2-methyl-propyl)-amine

HRID 2266069Notes

Reaction equation

[CH:1]([CH:4]([N:8]=[CH:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=1OC)[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[CH:22]([Li])([CH3:24])[CH3:23]>C1COCC1>[CH:22]([C:11]1[CH:12]=[C:13]([O:18][CH3:19])[C:14]([O:16][CH3:17])=[CH:15][C:10]=1[CH:9]=[N:8][CH:4]([CH:1]([CH3:2])[CH3:3])[CH:5]([CH3:6])[CH3:7])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (1-isopropyl-2-methyl-propyl)-(2,4,5-trimethoxy-benzylidene)-amine (1.024 g, 3.5 mmol) in 35 ml THF at −78° C. was added isopropyllithium (6.0 mL, 0.7 M in pentane) drop-wise over 5 minutes. The solution was allowed to stir 30 min at −78° C. After warming to room temperature over 45 minutes the mixture was quenched by the addition of 5 mL of 10% NH4Cl and concentrated in vacuo. 100 mL of H2O was added and the mixture was extracted with ethyl acetate, washed with H2O and then brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give (2-isopropyl4,5-dimethoxy-benzylidene)-(1-isopropyl-2-methyl-propyl)-amine as a yellow oil.

Workup

temperatureAfter warming to room temperature over 45 minutes the mixture
customwas quenched by the addition of 5 mL of 10% NH4Cl
concentrationconcentrated in vacuo
addition100 mL of H2O was added
extractionthe mixture was extracted with ethyl acetate
washwashed with H2O
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f418c2e0a9e94faea33b4ddd580924d5
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858632B2

Reaction notes

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