Hydrochloric Acid → HCID 18368932, compound

HRID 2280410Notes

Reaction equation

HRID 2280410 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:11](Cl)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].[F:18][CH2:19][C:20]#[N:21].Cl>O1CCCC1>[F:18][CH:19]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:20]#[N:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10420Acetonitrile, fluoro-HCID 62493Pivaloyl chlorideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 18368932HCID 18368932, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium hexamethyldisilazide (LHMDS) in tetrahydrofuran (THF) (1M, 33.9 mL, 2 equiv) was added dropwise to a chilled (−78° C.) solution of pivaloyl chloride (2.04 g, 1 equiv) and FCH2CN (1.00 g, 1 equiv) in THF (50 mL). The mixture was allowed to warm to room temperature and 1 N HCl was added dropwise until the solution was pH=2. The mixture was concentrated in vacuo to provide the title compound (2.40 g, 99% yield).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e7a4befb99a24bb6b2cb9d60b4f7361c
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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