Hydrochloric Acid → HCID 86713144, compound

HRID 713622Notes

Reaction equation

HRID 713622 reaction equation
[OH:1][C:2]1([C:12]#[C:13]/[C:14](/[C:21]([F:24])([F:23])[F:22])=[CH:15]\[C:16]([O:18]CC)=[O:17])[C:7]([CH3:9])([CH3:8])[CH2:6][C:5](=[O:10])[CH:4]=[C:3]1[CH3:11].[OH-].[Na+].Cl>O.O1CCCC1>[OH:1][C:2]1([C:12]#[C:13]/[C:14](/[C:21]([F:22])([F:23])[F:24])=[CH:15]\[C:16]([OH:18])=[O:17])[C:7]([CH3:8])([CH3:9])[CH2:6][C:5](=[O:10])[CH:4]=[C:3]1[CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86713140HCID 86713140, compound

Product 1

HCID 86713144HCID 86713144, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a round-bottom flask, ethyl (2E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)pent-2-en-4-ynoate (130 mg, 0.38 mmol) was dissolved in a mixture of water and tetrahydrofuran, and sodium hydroxide (38 mg, 0.94 mmol) was then added. The resulting reaction mixture was stirred under reflux for 2 h and, after cooling to room temperature, acidified with aqueous hydrochloric acid. The aqueous phase was repeatedly extracted thoroughly with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated under reduced pressure. By final column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient), (2E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)pent-2-en-4-ynoic acid (40 mg, 32% of theory) was obtained in the form of a colorless solid. 1H-NMR (400 MHz, CDCl3 δ, ppm) 10.14 (br. s, 1H, OH), 6.70 (s, 1H), 5.92 (s, 1H), 2.61 (d, 1H), 2.43 (d, 1H), 2.30 (br. s, 1H, OH), 2.16 (s, 3H), 1.28 (s, 3H), 1.13 (s, 3H).

Workup

  1. additionwas then added
  2. customThe resulting reaction mixture
  3. temperatureunder reflux for 2 h
  4. extractionThe aqueous phase was repeatedly extracted thoroughly with dichloromethane
  5. dry with materialthe combined organic phases were then dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customBy final column chromatography purification of the resulting crude product (ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-dbeeef0a8edb4e5fb1a589e8c027dcd4
Source dataset
uspto-grants-2015_11
Patent number
US09185914B2

Reaction notes

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