Tert-butyl 2-(2-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate → tert-Butyl 2-(2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate
Reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1C=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:33](C1C=C(C23CCC(CC(O)=O)(CC2)CO3)C=CC=1)C1C=CC=CC=1.O1CCCCC1OC1C=C(C23CCC(CC(OC)=O)(CC2)CO3)C=CC=1>>[O:33]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:1][C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1Participants
Reactant 3
Product 1
Procedure
tert-Butyl 2-(2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate was prepared using a procedure analogous to tert-butyl 2-(2-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate except that 2-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid was replace with methyl 2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate. The title compound was obtained (1 g, 2.24 mmol, 91% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 7.23-7.19 (m, 1H), 7.12-7.09 (m, 1H), 7.02-6.98 (m, 1H), 6.93 (ddd, J=8.3, 2.5, 0.8 Hz, 1H), 5.43 (t, J=3.3 Hz, 1H), 5.31 (s, 1H), 3.94 (s, 2H), 3.88-3.86 (m, 2H), 3.63-3.54 (m, 3H), 2.05-1.99 (m, 5H), 1.88-1.82 (m, 2H), 1.75-1.69 (m, 5H), 1.69-1.56 (m, 4H), 1.55-1.51 (m, 2H), 1.50 (s, 9H).
Workup
- customtert-Butyl 2-(2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate was prepared
Sources & evidence
- ORD record
- ord-cda370bad1d94fefaae80d8366c0c111
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962660B2
Reaction notes
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