Hexane → HCID 10523464, compound

HRID 1957775Notes

Reaction equation

[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.CCCCCC.[CH3:21][Sn:22](Cl)([CH3:24])[CH3:23]>C1COCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([NH:6][C:7](=[O:12])[C:8]([CH3:10])([CH3:11])[CH3:9])=[C:4]([Sn:22]([CH3:24])([CH3:23])[CH3:21])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-chloro N-pivaloylaniline* (2.11 g, 10 mmol) in 30 ml of dry THF was cooled in an ice bath under an atmosphere of nitrogen. Then an hexane solution of 1.6M of n-Buli (15.625 ml, 25 mmol) was added dropwise. After stirring at 0° C. for 2.5 h, trimethyltin chloride (2.19 g, 11 mmol) dissolved in dry THF (8 ml) was added within 20 min at 0° C. The reaction was then stirred for 2 h at 0° C. and for 16 h at room temperature, quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to dryness. The residue was purified by flash chromatography on silica gel (di-isopropylether: petroleum ether 40°/70°=10:23) to yield 4-chloro-2-trimethylstannyl-N-pivaloylaniline as a white solid 3.1 g; 82.9%; m.p. 169°-172° C.).

Workup

additionwas added within 20 min at 0° C
stirringThe reaction was then stirred for 2 h at 0° C. and for 16 h at room temperature
customquenched with water
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
customdried
concentrationconcentrated to dryness
customThe residue was purified by flash chromatography on silica gel (di-isopropylether: petroleum ether 40°/70°=10:23)

Sources & evidence

ORD record: ord-5efb4d34ac3b4c9fa0f9c6cec3b0873a
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05786508

Reaction notes

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