Chlorotrimethylsilane → HCID 22668873, compound

HRID 395401Notes

Reaction equation

C([Li])CCC.C(NC(C)C)(C)C.[F:13][C:14]([F:36])([F:35])[C:15]1[C:20]([C:21]([O:23][CH2:24]C)=[O:22])=[CH:19][C:18]([C:26]([O:28][CH2:29]C)=[O:27])=[C:17]([C:31]([F:34])([F:33])[F:32])[N:16]=1.Cl[Si:38]([CH3:41])([CH3:40])[CH3:39]>CCCCCC.C1COCC1.O>[F:13][C:14]([F:36])([F:35])[C:15]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([Si:38]([CH3:41])([CH3:40])[CH3:39])[C:18]([C:26]([O:28][CH3:29])=[O:27])=[C:17]([C:31]([F:34])([F:33])[F:32])[N:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To 10 ml of dry THF at −78° C. was added 8.4 ml (0.012 mol) of 1.55 M n-butyllithium in hexane followed by 1.21 g (1.7 ml, 0.012 mol) of diisopropylamine. After stirring at −78° C. for 30 min, a solution of 3.59 g (0.01 mol) of diethyl 2,6-bis(trifluoromethyl)-3,5-pyridine-dicarboxylate (prepared by the procedure similar to example 1 of U.S. Pat. No. 4,692,184) in 10 ml of dry THF was added. The reaction turned dark red and after stirring at −78° C. for 10 min, 4.4 g (0.05 mol) of chlorotrimethylsilane was added. The reaction was warmed to room temperature, stirred for 30 min and then was poured into 0° C. water, extracted with ether, dried (MgSO4) and concentrated in vacuo. The residue was purified by HPLC (1:20 EtOAc:hexane) affording 2.09 g of the product as a light yellow oil which crystallized upon standing: mp 29-31° C.

Workup

stirringafter stirring at −78° C. for 10 min
temperatureThe reaction was warmed to room temperature
stirringstirred for 30 min
extractionextracted with ether
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by HPLC (1:20 EtOAc:hexane)

Sources & evidence

ORD record: ord-0a2db15f0cdc4200b6df9be8bde2d405
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605624B1

Reaction notes

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