Acetone → (3E,5E)-5-Fluoro-6-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-3,5-dien-2-one

HRID 1883279Notes

Reaction equation

HRID 1883279 reaction equation
[F:1]/[C:2](=[C:5](/[C:8]1[C:17]([O:18][CH2:19][O:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:23])([CH3:22])[CH2:13][CH2:12][C:11]([CH3:25])([CH3:24])[C:10]=2[CH:9]=1)\[CH2:6][CH3:7])/[CH:3]=O.[OH-].[Na+].[CH3:28][C:29]([CH3:31])=[O:30]>>[F:1]/[C:2](=[C:5](/[C:8]1[C:17]([O:18][CH2:19][O:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:22])([CH3:23])[CH2:13][CH2:12][C:11]([CH3:24])([CH3:25])[C:10]=2[CH:9]=1)\[CH2:6][CH3:7])/[CH:3]=[CH:28]/[C:29](=[O:30])[CH3:31]

Participants

4

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 60098606(E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enal2×

Product 1

HCID 12146420(3E,5E)-5-Fluoro-6-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-3,5-dien-2-oneYield 95%

Procedure

To a solution of (E)-2-fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enal (Intermediate 17, 880 mg, 2.5 mmol) in acetone (10 mL) was added 1M NaOH (7.5 mL) at 0° C. The mixture was stirred for 5 h, quenched with 2M H2SO4 (10 mL), and was stirred for 30 min. The mixture was then extracted with EtOAc (×3). The combined organic layer was washed successively with brine, NaHCO3, was dried over MgSO4 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 yellow solid (930 mg, 95%).

Workup

  1. customquenched with 2M H2SO4 (10 mL)
  2. stirringwas stirred for 30 min
  3. extractionThe mixture was then extracted with EtOAc (×3)
  4. washThe combined organic layer was washed successively with brine, NaHCO3
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (5% EtOAc-hexane)

Sources & evidence

ORD record
ord-34c72f44d0ec437887d43242839f8029
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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