Hydrochloric Acid → HCID 86619897, compound

HRID 1361559Notes

Reaction equation

HRID 1361559 reaction equation
[OH-].[K+].C1O[CH2:19][CH2:18]OCCOCCOCCOCCOC1.[CH2:21]([C:23]1[CH2:27][CH:26]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:24]=1)[CH3:22].C([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=O)C.Cl>C1COCC1>[C:28]([C:25]1[CH:26]=[C:27]([CH2:18][CH3:19])[C:23](=[C:21]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH3:22])[CH:24]=1)([CH3:30])([CH3:29])[CH3:31]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 206271323-tert-Butyl-1-ethylcyclopenta-1,3-diene

Product 1

HCID 86619897HCID 86619897, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 200 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock, 2.10 g (36.1 mmol) of potassium hydroxide pulverized in mortar, 1.15 g (4.35 mmol) of 18-crown-6 and 50 ml of dehydrated THF were charged under a nitrogen atmosphere. Thereto in a water bath, 3.35 g (22.3 mmol) of 1-ethyl-3-tert-butylcyclopentadiene was added dropwise over 10 minutes, and stirred for 4 hours. The solution was added with 12.5 ml of acetophenone dropwise over 8 minutes, and stirred for 20 hours at room temperature and for 6 hours under reflux. The reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with 150 ml of ether. The obtained organic layers were combined, washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated aqueous solution of sodium chloride. After the solution was dried over magnesium sulfate, the solvent was distilled away, and purified by column chromatography to obtain 1.38 g of a red orange liquid. The yield was 25%. Identification was done by 1H-NMR spectrum. The measurement results are shown as follows.

Workup

  1. customTo a 200 ml three-neck flask equipped with a magnetic stirrer chip
  2. additionwere charged under a nitrogen atmosphere
  3. stirringstirred for 20 hours at room temperature and for 6 hours
  4. temperatureunder reflux
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with 150 ml of ether
  7. washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated aqueous solution of sodium chloride
  8. dry with materialAfter the solution was dried over magnesium sulfate
  9. distillationthe solvent was distilled away
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-a7de8100b5ae49ccb8759a7d660aebf3
Source dataset
uspto-grants-2011_02
Patent number
US07879960B2

Reaction notes

Loading…