Dimethylformamide → 2,6-Dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

HRID 1514882Notes

Reaction equation

Br[C:2]1[C:15]([CH3:16])=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[CH3:17].[Li]CCCC.CN([CH:26]=[O:27])C>C1COCC1>[CH3:17][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:14]=[C:15]([CH3:16])[C:2]=1[CH:26]=[O:27]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1-[2-(4-bromo-3,5-dimethyl-phenoxy)-ethyl]-pyrrolidine (176 mg) in THF (5 mL) was added n-BuLi (1.36 mL, 1.0 M solution in hexane) at −78° C. The mixture was stirred at −78° C. for 30 min, allowed to warm up to −40° C. for 5 min, and then cooled down to at −78° C. After 20 min. DMF (0.24 mL) was added. The mixture was stirred at −78° C. for 30 min and then allowed to warm up to room temperature for 1 h. The reaction was quenched with saturated NH4Cl aqueous solution and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give 2,6-dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde: MS (m/z) 248 (M+1).

Workup

temperatureto warm up to −40° C. for 5 min
temperaturecooled down to at −78° C
waitAfter 20 min
stirringThe mixture was stirred at −78° C. for 30 min
temperatureto warm up to room temperature for 1 h
customThe reaction was quenched with saturated NH4Cl aqueous solution
extractionextracted with EtOAc
washThe organic extracts were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-31873e92ec6e47d283e84029681b3008
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

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