2-Methylthiophene → 1-(5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene

HRID 2608

반응식

HRID 2608 반응식
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Li]CCCC.[CH3:12][C:13]1([CH3:25])[C:22]2[C:17](=[CH:18][C:19]([Br:23])=[CH:20][CH:21]=2)[C:16](=O)[CH2:15][CH2:14]1>C1COCC1.CCOCC.C(OC(=O)C)C>[CH3:1][C:2]1[S:3][C:4]([C:16]2[C:17]3[C:22](=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=3)[C:13]([CH3:25])([CH3:12])[CH2:14][CH:15]=2)=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 111262-MethylthiopheneHCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2회HCID 178418339Butyllithium

생성물 1

HCID 186200621-(5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene수율 62.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21584169Diethylether ethylacetate용매

반응 조건

온도
0 °C

실험 절차

To a cold (-78° C.) solution of 2-methylthiophene (800 mg, 8.1 mmol) in THF (10 mL) was added n-BuLi (1.6M solution in hexane, 5 mL). The mixture was stirred for 1.5 hours and transferred to a cold (-78° C.) flask containing 3,4-dihydro-4,4-dimethyl-7-bromo-1(2H)-naphthalenone (Compound A, 1.63 g, 6.5 mmol), in THF (15 mL). The mixture was gradually warmed to 0° C. The reaction mixture was diluted with ether:ethylacetate (1:1, 80 mL), washed with water (10 mL), brine (10 mL), dried with MgSO4 and the solvent was removed by evaporation. The crude material was dissolved in dichloroethane (20 mL) and pTSA (40 mg) was added. The mixture was stirred at ambient temperature for 16 hours and at 50° C. for 4 hours. The reaction mixture was diluted with ether (150 mL), washed with aqueous 10% NaHCO3 (10 mL), brine (10 mL) and dried with MgSO4. Purification by chromatography on silica gel gave 1.35 g of the title compound as a white solid.

후처리

  1. customtransferred to a cold (-78° C.) flask
  2. washwashed with water (10 mL), brine (10 mL)
  3. dry with materialdried with MgSO4
  4. customthe solvent was removed by evaporation
  5. dissolutionThe crude material was dissolved in dichloroethane (20 mL)
  6. additionpTSA (40 mg) was added
  7. stirringThe mixture was stirred at ambient temperature for 16 hours and at 50° C. for 4 hours
  8. additionThe reaction mixture was diluted with ether (150 mL)
  9. washwashed with aqueous 10% NaHCO3 (10 mL), brine (10 mL)
  10. dry with materialdried with MgSO4
  11. customPurification by chromatography on silica gel

출처 및 근거

ORD 기록
ord-1181981a49704b02b7381620902d58eb
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728846

연결된 노트

불러오는 중…