tert-Butyl 2-(2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate → (E)-Methyl 5-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate

HRID 1855053Notes

Reaction equation

HRID 1855053 reaction equation
OC1C=C(C23CCC(CCOCC(OC(C)(C)C)=O)(CC2)CO3)C=CC=1.O1CCCCC1OC1C=C(C23CCC(CCOCC(OC(C)(C)C)=O)(CC2)CO3)C=CC=1.O1CCCCC1[O:65][C:66]1[CH:67]=[C:68]([C:72]23[CH2:79][CH2:78][C:75]([CH2:80][CH2:81]/[CH:82]=[CH:83]/[C:84]([O:86][CH3:87])=[O:85])([CH2:76][CH2:77]2)[CH2:74][O:73]3)[CH:69]=[CH:70][CH:71]=1>>[OH:65][C:66]1[CH:67]=[C:68]([C:72]23[CH2:77][CH2:76][C:75]([CH2:80][CH2:81]/[CH:82]=[CH:83]/[C:84]([O:86][CH3:87])=[O:85])([CH2:78][CH2:79]2)[CH2:74][O:73]3)[CH:69]=[CH:70][CH:71]=1

Participants

4

Reactant 3

HCID 90408312tert-Butyl 2-(2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetateHCID 90409110tert-Butyl 2-(2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetateHCID 90409249(E)-Methyl 5-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate

Product 1

HCID 90408703(E)-Methyl 5-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate

Procedure

(E)-Methyl 5-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate was prepared using a procedure analogous to tert-butyl 2-(2-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate except that tert-butyl 2-(2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethoxy)acetate was replaced with (E)-methyl 5-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate. The title compound was obtained (210 mg, 0.66 mmol, 89% yield) as a white solid. LCMS, [M−H]+=315.2. 1H NMR (500 MHz, CDCl3) δ 7.17 (t, J=8.0 Hz, 1H), 7.03-6.89 (m, 3H), 6.70 (ddd, J=8.0, 2.5, 1.0 Hz, 1H), 5.87 (dt, J=15.7, 1.5 Hz, 1H), 5.71 (s, 1H), 3.85 (s, 2H), 3.76 (s, 3H), 2.23-2.15 (m, 2H), 2.03 (dd, J=9.1, 4.7 Hz, 4H), 1.74-1.62 (m, 4H), 1.37-1.30 (m, 2H).

Workup

  1. custom(E)-Methyl 5-(1-(3-hydroxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pent-2-enoate was prepared

Sources & evidence

ORD record
ord-b40e57b5a8d8467ea389ad0d7e751f8b
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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