Dimethylformamide → Methyl 3-[(1E)-3-(methyloxy)-1-propen-1-yl]-1-naphthalenecarboxylate
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CC1(C)C(C)(C)OB(/[CH:24]=[CH:25]/[CH2:26][O:27][CH3:28])O1.CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>O.C(O)CC>[CH3:28][O:27][CH2:26]/[CH:25]=[CH:24]/[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
Methyl 3-bromo-1-naphthalenecarboxylate (1 eq.) and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (1.5 eq.) were combined in a 5:1 (v/v) mixture of DMF:n-PrOH (0.2 M). To this solution was then added trans-bis(triphenylphosphine) palladium(II) bromide (0.05 eq.) and the vessel was repeatedly evacuated and back-filled with nitrogen. Finally, 2 N aq. Na2CO3 (2 eq.) was added and the resulting biphasic suspension was heated at 90° C. for 8 h. The now black suspension was cooled to RT, diluted with water and extracted with 1:1 (v/v) hexanes:ether. The combined organic extracts were then washed further with 1 N aq. NaOH, 1 N aq. HCl, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the title compound as a red oil.
Workup
- additionback-filled with nitrogen
- temperatureThe now black suspension was cooled to RT
- extractionextracted with 1:1 (v/v) hexanes
- washThe combined organic extracts were then washed further with 1 N aq. NaOH, 1 N aq. HCl, water and brine
- dry with materialThis was then dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-d23c7bd5bfdc484d8c9d7ef3ef8f854b
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889714B2
Reaction notes
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