Ethyl Acrylate → Ethyl 3-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]propenoate

HRID 48167Notes

Reaction equation

[CH2:1]([C:3]([CH2:16]C)([CH3:15])[CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11](Br)=[CH:10][C:8]=2[N:9]=1)C.[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=[CH2:20].C(N(CC)C(C)C)(C)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][C:3]([CH3:1])([CH3:15])[CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([CH:20]=[CH:19][C:18]([O:22][CH2:23][CH3:24])=[O:21])=[CH:10][C:8]=2[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(2,2-diethylpropyl)-5-bromobenzoxazole (0.60 g, 0.00225 mol), ethyl acrylate (1.08 g, 0.0108 mol), palladium acetate (0.051 g, 0.00023 mol), trintolylphosphine (0.135 g,0.0045 mol) and N,N-diisopropylethylamine (0.585 g, 0.0045 mol) was heated at 100° C. for 6 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate:dichloromethane 3:97, to give ethyl 3-[2-(2,2-dimethylpropyl)benzoxazol-5-yl]propenoate (0.634 g).

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
filtrationfiltered
customthe filtrate was evaporated in vacuo
customThe residue was purified by flash column chromatography on silica gel
washeluting with ethyl acetate:dichloromethane 3:97

Sources & evidence

ORD record: ord-a632a874053e4fed82007d7d2fc4ef80
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703347B2

Reaction notes

Loading…