Carbon Dioxide → 5,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenecarboxylic acid

HRID 495930

반응식

HRID 495930 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=3)[C:11]([CH3:20])([CH3:19])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[C:26](=[O:28])=[O:27]>C1COCC1>[CH3:19][C:11]1([CH3:20])[CH2:10][CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[C:17]2[CH:16]=[C:15]([C:26]([OH:28])=[O:27])[CH:14]=[CH:13][C:12]1=2

참가 물질

5

반응물 3

HCID 280Carbon DioxideHCID 106876226-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene2회HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 105416825,6-Dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenecarboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-7-bromonaphthalene (Compound D) (250.0 mg, 0.764 mmol) in 2.0 ml of THF was cooled to −78° C. and 1.0 ml of t-butyllithium (1.68 mmol, 1.7 M solution in pentane) was added slowly. After stirring for 1 hour at −78° C. gaseous CO2 (generated by evaporation of Dry-Ice, and passed through a drying tube) was bubbled through the reaction for 1 hour. The solution was then allowed to warm to room temperature and the reaction was quenched by the addition of 10% HCl. Extraction with EtOAc was followed by washing the combined organic layers with H2O and saturated aqueous NaCl, and drying over MgSO4. Removal of the solvents under reduced pressure and washing of the solid with hexanes afforded the title compound as a colorless solid. 1H NMR (CDCl3): δ 7.94 (1H, dd, J=1.8, 8.1 Hz), 7.76 (1H, d, J=1.8 Hz), 7.45 (1H, d, J=8.1 Hz), 7.24 (4H, m), 6.01 (1H, t, J=4.7 Hz), 2.40 (3H, s), 2.36 (2H, d, J=4.7 Hz), 1.35 (6H, s).

후처리

  1. customwas bubbled through the reaction for 1 hour
  2. customthe reaction was quenched by the addition of 10% HCl
  3. extractionExtraction with EtOAc
  4. washby washing the combined organic layers with H2O and saturated aqueous NaCl
  5. dry with materialdrying over MgSO4
  6. customRemoval of the solvents under reduced pressure
  7. washwashing of the solid with hexanes

출처 및 근거

ORD 기록
ord-a18232890d6540fcb83e2eb2b39ab053
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06942980B1

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