Hydrochloric Acid → HCID 86759479, compound

HRID 1883282Notes

Reaction equation

HRID 1883282 reaction equation
[CH2:1]([O:3][C:4](=[O:34])/[C:5](/[F:33])=[C:6](\[CH3:32])/[CH:7]=[CH:8]/[C:9](/[F:31])=[C:10](\[C:13]1[C:22]([O:23]COC)=[CH:21][C:20]2[C:19]([CH3:28])([CH3:27])[CH2:18][CH2:17][C:16]([CH3:30])([CH3:29])[C:15]=2[CH:14]=1)/[CH2:11][CH3:12])[CH3:2].Cl>CC(O)C.C1COCC1>[CH2:1]([O:3][C:4](=[O:34])/[C:5](/[F:33])=[C:6](\[CH3:32])/[CH:7]=[CH:8]/[C:9](/[F:31])=[C:10](\[C:13]1[C:22]([OH:23])=[CH:21][C:20]2[C:19]([CH3:27])([CH3:28])[CH2:18][CH2:17][C:16]([CH3:30])([CH3:29])[C:15]=2[CH:14]=1)/[CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12146422(2Z,4E,6E)-2,6-difluoro-7-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid ethyl ester

Product 1

HCID 86759479HCID 86759479, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2Z,4E,6E)-2,6-difluoro-7-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid ethyl ester (Compound 19, 2-E/Z mixture, 387 mg, 0.81 mmol) in i-PrOH (2 mL) and THF (2 mL) was added conc. HCl (1.0 mL). The mixture was stirred at ambient temperature for overnight, 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 (5% EtOAc-hexane) to give the title compound as a 2-E/Z mixture (370 mg, 100%). This mixture was used directly for the next alkylation reaction.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (5% EtOAc-hexane)

Sources & evidence

ORD record
ord-b224b1e4b9ef4131b2485b60decdbcec
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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