Water → HCID 86713148, compound

HRID 713629Notes

Reaction equation

HRID 713629 reaction equation
[CH:1]1(/[C:4](/[CH:11]=[CH:12]/[C:13]2([OH:31])[C:24]([CH3:29])([C:25]([F:28])([F:27])[F:26])[CH2:23][C:16]3(OC(C)C(C)[O:17]3)[CH:15]=[C:14]2[CH3:30])=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.O>CC(C)=O.Cl>[CH:1]1(/[C:4](/[CH:11]=[CH:12]/[C:13]2([OH:31])[C:24]([CH3:29])([C:25]([F:28])([F:27])[F:26])[CH2:23][C:16](=[O:17])[CH:15]=[C:14]2[CH3:30])=[CH:5]/[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 962WaterHCID 86713146HCID 86713146, compound

Product 1

HCID 86713148HCID 86713148, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 180AcetoneSolvent

Procedure

Ethyl (2Z,4E)-3-cyclopropyl-5-[8-hydroxy-2,3,7,9-tetramethyl-9-(trifluoromethyl)-1,4-dioxaspiro[4.5]dec-6-en-8-yl]penta-2,4-dienoate (40 mg, 0.09 mmol) was dissolved in acetone (4 ml) under argon in a round-bottom flask, and a few drops of conc. hydrochloric acid were added. The resulting reaction solution was stirred at room temperature for 4 h and then water was added. After removing acetone under reduced pressure, the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient), ethyl (2Z,4E)-3-cyclopropyl-5-[1-hydroxy-2,6-dimethyl-4-oxo-6-(trifluoromethyl)cyclohex-2-en-1-yl]penta-2,4-dienoate (15 mg, 45% of theory) was obtained in the form of a colorless oil. 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.88 (d, 1H), 6.37 (d, 1H), 6.01 (s, 1H), 5.64 (s, 1H), 4.17 (q, 2H), 2.92 (d, 1H), 2.52 (d, 1H), 2.39 (br. s, 1H, OH), 1.98 (s, 3H), 1.59 (m, 1H), 1.30 (t, 3H), 1.28 (s, 3H), 0.88 (m, 2H), 0.59 (m, 2H).

Workup

  1. customThe resulting reaction solution
  2. customAfter removing acetone under reduced pressure
  3. extractionthe aqueous phase was extracted repeatedly with dichloromethane
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customBy column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-6efd1a16b37b4b41875e4854007a4090
Source dataset
uspto-grants-2015_11
Patent number
US09185914B2

Reaction notes

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