Hydrochloric Acid → ethyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate

HRID 713621노트

반응식

HRID 713621 반응식
[OH:1][C:2]1(/[CH:17]=[CH:18]/[C:19](/[C:26]([F:29])([F:28])[F:27])=[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].Cl.O>CC(C)=O>[OH:1][C:2]1(/[CH:17]=[CH:18]/[C:19](/[C:26]([F:27])([F:28])[F:29])=[CH:20]\[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:13]([CH3:14])([CH3:15])[CH2:12][C:5](=[O:6])[CH:4]=[C:3]1[CH3:16]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86713142ethyl (2E,4E)-5-(8-hydroxy-2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-yl)-3-(trifluoromethyl)penta-2,4-dienoate

생성물 1

HCID 86713143ethyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate수율 64.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Ethyl (2E,4E)-5-(8-hydroxy-2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-yl)-3-(trifluoromethyl)penta-2,4-dienoate (150 mg, 0.36 mmol) was dissolved in acetone (5 ml) under argon in a round-bottom flask, and 10% strength hydrochloric acid was added. The resulting reaction solution was stirred at room temperature for 40 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 column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient), ethyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate (80 mg, 61% of theory) was obtained in the form of a colorless oil. 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.55 (d, 1H), 6.37 (d, 1H), 6.33 (s, 1H), 5.97 (s, 1H), 4.25 (q, 2H), 2.47 (d, 1H), 2.34 (d, 1H), 1.92 (s, 3H), 1.90 (br. s, 1H, OH), 1.33 (t, 3H), 1.11 (s, 3H), 1.02 (s, 3H).

후처리

  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)

출처 및 근거

ORD 기록
ord-d4f5ba8ab9a64e378046b71beb8ebf2c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09185914B2

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