2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol → 3-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanal

HRID 1855054Notes

Reaction equation

HRID 1855054 reaction equation
O1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH:24]=[O:25])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1.O1CCCC[CH:27]1OC1C=C(C23CCC(CCO)(CC2)CO3)C=CC=1.O(C1C=C(C23CCC(CCO)(CC2)CO3)C=CC=1)C1C=CC=CC=1>>[O:7]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH:24]=[O:25])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:27]=1

Participants

4

Reactant 3

HCID 904081342-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanolHCID 904083923-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanalHCID 904088772-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol

Product 1

HCID 904083183-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanal

Procedure

3-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanal (clear oil) was prepared using a procedure analogous to 3-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanal except that 2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol was replaced with 2-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol. LCMS, [M−H]+=335.2. 1H NMR (500 MHz, CDCl3) δ 9.78 (t, J=1.5 Hz, 1H), 7.34-7.23 (m, 3H), 7.14-7.03 (m, 3H), 7.01-6.95 (m, 2H), 6.87-6.81 (m, 1H), 3.81-3.78 (m, 2H), 2.43-2.36 (m, 2H), 2.09-1.94 (m, 4H), 1.69-1.58 (m, 4H), 1.54-1.47 (m, 2H).

Sources & evidence

ORD record
ord-f2358af6fd7e450da216ab72954fd453
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

Loading…