Trimethylsulfonium iodide → 2-(3-(2-(7-Chloroquinolin-2-yl)cyclopropyl)phenyl)1,3-dioxolane

HRID 22597

Reaction equation

[I-].C[S+](C)C.[CH2:6]([Li])CCC.[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH:22]=[CH:23][C:24]3[CH:25]=[C:26]([CH:30]4[O:34][CH2:33][CH2:32][O:31]4)[CH:27]=[CH:28][CH:29]=3)=[N:19]2)=[CH:14][CH:13]=1>C1COCC1>[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH:22]3[CH2:6][CH:23]3[C:24]3[CH:25]=[C:26]([CH:30]4[O:34][CH2:33][CH2:32][O:31]4)[CH:27]=[CH:28][CH:29]=3)=[N:19]2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 21 °C

Procedure

To a solution of trimethylsulfonium iodide (2.128 g, 10.4 mmoles) in 20 mL of anhydrous THF at -10° C. was added dropwise a solution of n-butyllithium 1.6M in hexanes (4.9 mL, 0.75 equiv.). Then the temperature was raised to 21° C. for 2 hours. To this mixture cooled to 0° C., the alkene (step 2) (967 mg, 2.86 mmoles) in 5 mL THF was added and the solution stirred overnight. Hydrolysis with 25% aqueous NH4OAc, extraction with EtOAc and flash chromatography on silica using EtOAc:toluene 2.5:97.5 afforded the title compound.

Workup

temperatureTo this mixture cooled to 0° C.
customHydrolysis
extractionwith 25% aqueous NH4OAc, extraction with EtOAc and flash chromatography on silica

Sources & evidence

ORD record: ord-c503a7df0f134bb2832625ca3ad201ea
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05428171

Linked notes

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