Acetonitrile → HCID 67958805, compound

HRID 2280424Notes

Reaction equation

[C:1](#[N:3])[CH3:2].C([Li])CCC.[Si:9]([O:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C1COCC1>[Si:9]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22](=[O:23])[CH2:2][C:1]#[N:3])=[CH:25][CH:26]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: -78 °C

Procedure

To a chilled (−78° C.) solution of acetonitrile (MeCN) (1.13 mL, 4 equiv) in THF (54 mL) was added butyllithium (BuLi) (1.62 mL, 10 M in hexanes, 3 equiv) dropwise, keeping the temperature under −60° C. The mixture was stirred for 15 minutes at −78° C. A solution of 4-(((tert-butyldimethylsilyl)oxy)methyl)benzoyl chloride (1.44 g) in THF (5 mL) was slowly added, and the reaction mixture was stirred at −78° C. for 45 minutes. The reaction was then quenched with aqueous ammonium chloride and diluted with EtOAc. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate, and concentrated onto silica gel. Purification by silica chromatography (9:1 hexanes:EtOAc to EtOAc) provided the title compound (370 mg, 24% yield) and the de-silylated product (330 mg).

Workup

customunder −60° C
stirringthe reaction mixture was stirred at −78° C. for 45 minutes
customThe reaction was then quenched with aqueous ammonium chloride
additiondiluted with EtOAc
customThe phases were separated
washthe organic phase was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated onto silica gel
customPurification by silica chromatography (9:1 hexanes:EtOAc to EtOAc)

Sources & evidence

ORD record: ord-12f07227daa3472baedd850ab3c8581a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139532B2

Reaction notes

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