Trimethylsilylmethyl Azide → HCID 67496021, compound

HRID 402352

Reaction equation

HRID 402352 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[CH3:2].[N:15]([CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[N+:16]=[N-:17]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[N:15]([CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:16]=[N:17][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1)=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 150751Trimethylsilylmethyl Azide2×HCID 12027755ETHYL 3-(4-FLUOROPHENYL)PROPIOLATE

Product 1

HCID 67496021HCID 67496021, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (4-fluoro-phenyl)-propynoic acid ethyl ester (1.45 g, 7.55 mmol) in benzene (25 mL) was added azidomethyl-trimethyl-silane (1.17 g, 9.05 mmol) and the reaction mixture was refluxed under nitrogen for 72 h. A subsequent batch of azidomethyl-trimethyl-silane (0.29 g, 2.26 mmol) was added and refluxing was continued for 5 h. The mixture was then evaporated and purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (1.0 g, 41%) as a yellow oil. MS: m/e=322.2 [M+H]+.

Workup

  1. temperaturethe reaction mixture was refluxed under nitrogen for 72 h
  2. temperaturerefluxing
  3. customThe mixture was then evaporated
  4. custompurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-9b8ceadd3ad94883a7a2cfa22d3e7a9e
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Linked notes

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