1,2,3-Trimethylindene → HCID 13280229, 화합물

HRID 871188노트

반응식

HRID 871188 반응식
C[C:2]1([OH:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH3:11])[CH:3]1[CH3:12].CC1C2C(=CC=CC=2)C(C)=C1C>C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:12][CH:3]1[CH:4]([CH3:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:13]

참가 물질

5

반응물 2

HCID 5887781,2,3-TrimethylindeneHCID 68862969HCID 68862969, 화합물

생성물 1

HCID 13280229HCID 13280229, 화합물수율 45.1%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

실험 절차

In a 1 liter three necked round bottomed flask fitted with a magnetic stirring apparatus and a reflux condenser 2,3-dimethyl-1-indanone (34) (19.2 g, 0.12 mol) was dissolved in dry diethyl ether (300 ml) under an argon atmosphere. Methyllithium (46.3 ml, 3 M solution in diethoxymethane, 0.14 mol) was added dropwise via a syringe and the mixture was refluxed overnight. The mixture was cooled to 0° C. and a solution of saturated ammonium chloride (100 ml) was added dropwise through the top of the condenser. The mixture was transferred into a separation funnel, the organic layer was washed with water (3×100 ml), dried over magnesium sulfate and filtered. The ether was removed under reduced pressure to afford the raw 1,2,3-trimethyl-1-indanol (19.34 g, 92%) as a yellow liquid which was used for the next step without further purification. Toluene (300 ml) was added to the raw 1,2,3-trimethyl-1-indanol (19.34 g, 0.11 mol) and the solution was transferred into a 500 ml round bottomed flask fitted with a Dean-Stark trap and a magnetic stirring apparatus. p-Toluene sulfonic acid (50 mg, 0.26 mmol) was added and the solution refluxed overnight. After completion of the removal of the water the excess toluene was removed via distillation through the Dean-Stark arm, the residue was cooled to ambient temperature, diluted with diethyl ether (100 ml), washed with a saturated solution of sodium bicarbonate (3×100 ml), dried over magnesium sulfate and filtered. After removal of the solvent in vacuo, the liquid was purified via column-chromatography [(SiO2, 50×9 cm) eluent: cyclohexane:ethylacetate (10:1)] to afford two fractions: 1,2,3-Trimethylindene (37) (8.92 g, 51%) as a pale yellow liquid Rf 0.41; (34) (7.94 g, 45%) (starting material) was obtained as a dark yellow liquid.

후처리

  1. customwas used for the next step without further purification
  2. customthe solution was transferred into a 500 ml round bottomed flask
  3. customfitted with a Dean-Stark trap
  4. temperaturethe solution refluxed overnight
  5. customAfter completion of the removal of the water the excess toluene
  6. customwas removed via distillation through the Dean-Stark arm
  7. additiondiluted with diethyl ether (100 ml)
  8. washwashed with a saturated solution of sodium bicarbonate (3×100 ml)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customAfter removal of the solvent in vacuo
  12. customthe liquid was purified via column-chromatography [(SiO2, 50×9 cm) eluent: cyclohexane:ethylacetate (10:1)]
  13. customto afford two fractions

출처 및 근거

ORD 기록
ord-32d9a18245d547eb8bf2cf5f139f28fa
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969624B2

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