Water → HCID 86713139, compound

HRID 713618Notes

Reaction equation

HRID 713618 reaction equation
[OH:1][C:2]1(/[CH:17]=[CH:18]/[C:19](/[CH2:26][CH2:27][CH3:28])=[CH:20]\[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:13]([CH3:15])([CH3:14])[CH2:12][C:5]2(OC(C)C(C)[O:6]2)[CH:4]=[C:3]1[CH3:16].O>CC(C)=O.Cl>[OH:1][C:2]1(/[CH:17]=[CH:18]/[C:19](/[CH2:26][CH2:27][CH3:28])=[CH:20]\[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:13]([CH3:15])([CH3:14])[CH2:12][C:5](=[O:6])[CH:4]=[C:3]1[CH3:16]

Participants

5

Reactant 2

HCID 962WaterHCID 86713137HCID 86713137, compound

Product 1

HCID 86713139HCID 86713139, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 180AcetoneSolvent

Procedure

Ethyl (2Z)-3-[(E)-2-(8-hydroxy-2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]-dec-6-en-8-yl)vinyl]hex-2-enoate (180 mg, 0.46 mmol) was dissolved in acetone (5 ml) under argon in a round-bottom flask, and 3 drops of conc. hydrochloric acid were added. The resulting reaction solution was stirred at room temperature for 30 minutes, and water was then 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 final column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient), ethyl (2Z)-3-[(E)-2-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)vinyl]hex-2-enoate (114 mg, 74% of theory) was obtained in the form of a colorless oil. 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.77 (d, 1H), 6.15 (d, 1H), 6.05 (s, 1H), 5.93 (s, 1H), 4.19 (q, 2H), 2.96 (br. s, 1H, OH), 2.47 (d, 1H), 2.31 (d, 1H), 2.24 (t, 2H), 1.92 (s, 3H), 1.58 (m, 2H), 1.27 (t, 3H), 1.24 (s, 3H), 1.12 (s, 3H), 0.92 (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 final column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-810a60adcbc045b6bdc624b27ca67628
Source dataset
uspto-grants-2015_11
Patent number
US09185914B2

Reaction notes

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