Hydrochloric Acid → HCID 10388100, compound

HRID 1883272Notes

Reaction equation

C([O:3][C:4](=[O:33])/[C:5](/[F:32])=[C:6](\[CH3:31])/[CH:7]=[CH:8]/[C:9](/[F:30])=[C:10](\[C:12]1[C:21]([O:22][CH2:23][CH2:24][CH3:25])=[CH:20][C:19]2[C:18]([CH3:27])([CH3:26])[CH2:17][CH2:16][C:15]([CH3:29])([CH3:28])[C:14]=2[CH:13]=1)/[CH3:11])C.[OH-].[Na+].Cl>CCO>[F:32]/[C:5](=[C:6](/[CH3:31])\[CH:7]=[CH:8]\[C:9](\[F:30])=[C:10](/[C:12]1[C:21]([O:22][CH2:23][CH2:24][CH3:25])=[CH:20][C:19]2[C:18]([CH3:27])([CH3:26])[CH2:17][CH2:16][C:15]([CH3:29])([CH3:28])[C:14]=2[CH:13]=1)\[CH3:11])/[C:4]([OH:33])=[O:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (2Z,4E,6E)-2,6-difluoro-3-methyl-7-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-2,4,6-trienoic acid ethyl ester (Compound 10, 82 mg, 0.18 mmol) in EtOH (2 mL) was added 1M NaOH (1.0 mL). The mixture was heated to 60° C. for 2 h and was cooled to ambient temperature, acidified with 1M HCl, and extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (50% EtOAc-hexane) to give the title compound as a pale yellow solid (56 mg, 73%).

Workup

temperaturewas cooled to ambient temperature
extractionextracted with EtOAc (×3)
washThe combined organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel (50% EtOAc-hexane)

Sources & evidence

ORD record: ord-91b6ab371c2744079bd8cdf87f73c26e
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759547B1

Reaction notes

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