Hydrochloric Acid → HCID 86594542, compound

HRID 1816428Notes

Reaction equation

C([O:3][C:4](=[O:31])/[CH:5]=[C:6](\[CH3:30])/[CH:7]=[CH:8]/[CH:9]=[C:10](/[C:15]1[C:24]([OH:25])=[CH:23][C:22]2[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=2[CH:16]=1)\[C:11]([F:14])([F:13])[F:12])C.O[Li].O.Cl>CCO.C1COCC1.O>[F:12][C:11]([F:13])([F:14])/[C:10](/[C:15]1[C:24]([OH:25])=[CH:23][C:22]2[C:21]([CH3:26])([CH3:27])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=2[CH:16]=1)=[CH:9]\[CH:8]=[CH:7]\[C:6](\[CH3:30])=[CH:5]\[C:4]([OH:31])=[O:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (2E,4E,6Z)-8,8,8-trifluoro-7-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-octa-2,4,6-trienoic acid ethyl ester (Intermediate 5, 100 mg, 0.23 mmol) in EtOH-THF-H2O (2 mL, 2 mL, 0.3 mL) was added LiOH.H2O 29 mg, 0.69 mmol). The mixture was heated to 40° C. for 4 h and was cooled to ambient temperature, acidified with 1M HCl and extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (40% EtOAc-hexane) to give a 3:2 mixture of the title compound and its 13-Z isomer (91 mg). Further purification by HPLC (20% EtOAc-hexane) afforded the title compound as a white solid (39 mg, 42%).

Workup

temperaturewas cooled to ambient temperature
extractionextracted with EtOAc (×3)
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel (40% EtOAc-hexane)
customto give

Sources & evidence

ORD record: ord-58fd767609f04575bab3226d15fc6a7e
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884820B2

Reaction notes

Loading…