Benzene, 1-chloro-4-ethynyl- → HCID 71255724, compound

HRID 2202148Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)=[O:19]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:18]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1-chloro-4-ethynylbenzene (2.76 g, 20.20 mmol) in THF (50 mL) at −78° C. was added 2.5 M butyllitium (8.81 ml, 22.03 mmol in hexane) and stirred for 1 h at −78° C. tert-Butyl 4-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate (Compound 1.2, 5 g, 18.36 mmol) was added. The mixture was stirred at −78° C. for 30 min, then warmed up to 0° C., stirred for another hour at the same temperature, and diluted with water. The organic layer was separated and the aqueous was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, and the drying agent was filtered off. The filtrate was concentrated. The residue was purified by silica gel column chromatography using gradient elution (5 to 30%, EtOAc/hexane). LC-MS m/z 292.06 [M−56+H]+.

Workup

additionwas added
temperaturewarmed up to 0° C.
stirringstirred for another hour at the same temperature
customThe organic layer was separated
extractionthe aqueous was extracted with ethyl acetate
dry with materialThe combined organic layers were dried over Na2SO4
filtrationthe drying agent was filtered off
concentrationThe filtrate was concentrated
customThe residue was purified by silica gel column chromatography
washelution (5 to 30%, EtOAc/hexane)

Sources & evidence

ORD record: ord-48e75d6d8e704b53aeabf7cef64777ea
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365539B2

Reaction notes

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