Hydrochloric Acid → Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acrylate
Reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([O:10]C2CCCCO2)[CH:7]=[C:6]([B:17]2[O:21]C(C)(C)[C:19](C)(C)[O:18]2)[C:3]=1C=O.C1N2[CH2:32][CH2:33]N(CC2)C1.Cl.[C:35]([O:39][CH2:40][CH3:41])(=[O:38])C=C>>[OH:21][B:17]1[C:6]2[CH:7]=[C:8]([OH:10])[CH:9]=[C:2]([CH3:1])[C:3]=2[CH:19]([C:32](=[CH2:33])[C:35]([O:39][CH2:40][CH3:41])=[O:38])[O:18]1Participants
Procedure
Into a 50-mL round-bottom flask was placed a solution of 2-methyl-4-(tetrahydro-2H-pyran-2-yloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (5 g, 14.45 mmol, 1.00 equiv) in ethyl acrylate (10 mL), then added DABCO (2.42 g, 21.61 mmol, 1.50 equiv). The resulting solution was stirred for 24 h at room temperature. The pH value of the solution was adjusted to 3 with HCl (3N) and stirred for 2 h at 30° C. The resulting solution was extracted with 3×50 mL of ethyl acetate. The organic layers were combined, washed with 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:1). This resulted in 3.0 g (75%) of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acrylate as a white solid.
Workup
- customInto a 50-mL round-bottom flask was placed
- stirringstirred for 2 h at 30° C
- extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
- washwashed with 2×20 mL of brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- washeluted with ethyl acetate/petroleum ether (1:1)
- customThis resulted in 3.0 g (75%) of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acrylate as a white solid
Sources & evidence
- ORD record
- ord-17662c6c6eb4427396dffafe72f24403
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343944B2
Reaction notes
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