Hydrochloric Acid → 3-Tert-butyl-6-phenyl-1,6-dimethyl-fulvene

HRID 1361562

반응식

HRID 1361562 반응식
[OH-].[K+].[CH2:3]1OCCOCCOCCOCCOCCOC1.[C:21]([C:25]1[CH2:29][CH:28]=[C:27](C)[CH:26]=1)([CH3:24])([CH3:23])[CH3:22].[C:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=O)[CH3:32].Cl>C1COCC1>[C:21]([C:25]1[CH:26]=[C:27]([CH3:28])[C:32](=[C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH3:3])[CH:29]=1)([CH3:24])([CH3:23])[CH3:22]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 153198441-Tert-butyl-3-methylcyclopenta-1,3-diene

생성물 1

HCID 866198983-Tert-butyl-6-phenyl-1,6-dimethyl-fulvene수율 241.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 100 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock, 1.50 g (25.8 mmol) of potassium hydroxide pulverized in mortar, 0.91 g (3.44 mmol) of 18-crown-6 and 45 ml of THF were charged under a nitrogen atmosphere. Thereto in a water bath, 2.70 g (16.0 mmol) of 1-tert-butyl-3-methylcyclopentadiene was added dropwise over 10 minutes and stirred for 3 hours. The solution was added with 11.33 g (94.3 mmol) of acetophenone dropwise over 10 minutes, and stirred for 22 hours. The reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with 200 ml of hexane. The separated 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 obtained product was purified by column chromatography to obtain 1.98 g of a red orange liquid. The yield was 52%. Identification was done by 1H-NMR spectrum and FD-mass analysis spectrum. The result of the 1H-NMR spectrum proved that the obtained compounds are mixture of isomers. The measurement results are shown as follows.

후처리

  1. customTo a 100 ml three-neck flask equipped with a magnetic stirrer chip
  2. additionwere charged under a nitrogen atmosphere
  3. stirringstirred for 22 hours
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with 200 ml of hexane
  6. washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water, and saturated aqueous solution of sodium chloride
  7. dry with materialAfter the solution was dried over magnesium sulfate
  8. customthe obtained product was purified by column chromatography

출처 및 근거

ORD 기록
ord-9253f567908543b0a4c5ab2fe33a27f8
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879960B2

연결된 노트

불러오는 중…