1,3-Butadiene → Methyl 3-chloro-4-(3,6-dihydro-[1,2]oxazin-2-yl)-benzoate

HRID 2222518Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N:12]=[O:13])[C:5]([O:7][CH3:8])=[O:6].[CH2:14]=[CH:15][CH:16]=[CH2:17]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH:16]=[CH:15][CH2:14][O:13]1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

1.00 g (5.01 mmol) methyl 3-chloro-4-nitroso-benzoate are placed in 10 ml chloroform and a freshly prepared solution of 1.10 g (20.3 mmol) butadiene in 6 ml chloroform is added dropwise with stirring at 0° C. The reaction mixture is stirred for 30 minutes at 0-10° C. and for 16 hours at ambient temperature, evaporated down i. vac. and purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate=19:1).

Workup

stirringThe reaction mixture is stirred for 30 minutes at 0-10° C. and for 16 hours at ambient temperature
customevaporated down i
customand purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate=19:1)

Sources & evidence

ORD record: ord-c3b244b2eea8414f9bfa9805341a69b2
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371743B2

Reaction notes

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