Trifluoroacetic acid → HCID 11406249, compound

HRID 2100180Notes

Reaction equation

CC([C:5]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[C:25]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)=[C:6]([CH3:10])[C:7]([O-:9])=[O:8])(C)C.C(O)(C(F)(F)F)=O>>[C:25]1(=[C:17]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[C:14]2[CH:15]=[CH:16][C:11](/[CH:5]=[C:6](\[CH3:10])/[C:7]([OH:9])=[O:8])=[CH:12][CH:13]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178460441HCID 178460441, compound

Product 1

HCID 11406249HCID 11406249, compoundYield 92.4%

Procedure

The general hydrolysis procedure described for 195 was followed. (1,1-dimethylethyl (2E/2Z)-3-{4-[cyclooctylidene(4-hydroxyphenyl)methyl]phenyl}-2-methyl-2-propenoate (214) (0.200 g, 0.46 mmol) was treated with TFA to afford 0.160 g (92%) of the title compound 215 as a mixture of E and Z (˜65:35) isomers. The pure E isomer was isolated by HPLC to afford the title compound 214 as a white solid. 1H NMR (300 MHz, CD3OD): δ 7.67 (s, 1H), 7.38 (br d, J=6.0 Hz, 2H), 7.22 (br, d, J=6.6 Hz, 2H), 7.00 (br d, J=6.6 Hz, 2H), 6.72 (br d, J=6.3 Hz, 2H), 2.31 (br s, 4H), 2.10 (s, 3H), 1.70 (br s, 2H), 1.58 (br s, 8H). LCMS (ESI): m/z 375 (M−H)−.

Workup

customThe general hydrolysis procedure

Sources & evidence

ORD record: ord-df7a9c1062bb4591b668877bfaa6c125
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569601B2

Reaction notes

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