Water → HCID 90085834, compound

HRID 713627Notes

Reaction equation

HRID 713627 reaction equation
[OH:1][C:2]1([C:20]#[C:21]/[C:22](/[C:29]([F:32])([F:31])[F:30])=[CH:23]\[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:13]([CH3:18])([C:14]([F:17])([F:16])[F:15])[CH2:12][C:5]2(OC(C)C(C)[O:6]2)[CH:4]=[C:3]1[CH3:19].O>CC(C)=O.Cl>[OH:1][C:2]1([C:20]#[C:21]/[C:22](/[C:29]([F:30])([F:31])[F:32])=[CH:23]\[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:13]([CH3:18])([C:14]([F:17])([F:16])[F:15])[CH2:12][C:5](=[O:6])[CH:4]=[C:3]1[CH3:19]

Participants

5

Reactant 2

HCID 962WaterHCID 90085833HCID 90085833, compound

Product 1

HCID 90085834HCID 90085834, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 180AcetoneSolvent

Procedure

Ethyl (2E)-5-[8-hydroxy-2,3,7,9-tetramethyl-9-(trifluormethyl)-1,4-dioxaspiro[4.5]dec-6-en-8-yl]-3-(trifluoromethyl)pent-2-en-4-ynoate (110 mg, 0.23 mmol) was dissolved in acetone (5 ml) under argon in a round-bottom flask, and 5 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 (2E)-5-[1-hydroxy-2,6-dimethyl-4-oxo-6-(trifluoromethyl)cyclohex-2-en-1-yl]-3-(trifluoromethyl)pent-2-en-4-ynoate (70 mg, 71% of theory) was isolated in the form of a colorless viscous oil. 1H-NMR (400 MHz, CDCl3 δ, ppm) 6.72/6.71 (s, 1H), 5.98/5.97 (s, 1H), 4.28/3.93 (q, 2H), 3.28 (br. s, 1H, OH), 3.00 (d, 1H), 2.66 (d, 1H), 2.21/2.18 (s, 3H), 1.49/1.37 (s, 3H), 1.32/1.09 (t, 3H).

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-2cad646fdbf74ecdbd9c52622417bdbb
Source dataset
uspto-grants-2015_11
Patent number
US09185914B2

Reaction notes

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