Carbon Dioxide → 1(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

HRID 2609

반응식

HRID 2609 반응식
[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=3)[C:10]([CH3:19])([CH3:18])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.CN([CH:33]=[O:34])C.C(=O)=O>C1COCC1.CCOCC>[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:33]=[O:34])[CH:15]=3)[C:10]([CH3:19])([CH3:18])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 8003PentaneHCID 186200621-(5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene2회HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 186200661(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a cold (-78° C.) solution of 1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound F, 1.35 g, 4.1 mmol), in THF (20 mL) was added t-BuLi in pentane (1.7M solution, 3.5 mL, 5.95 mmol). The reaction was stirred for 15 minutes and DMF (600 mg, 5.8 mmol) was added and dry-ice cooling was replaced with ice-water bath. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was diluted with ether (70 mL) and washed with water (5 mL), brine (5 mL) and dried with MgSO4. Solvent was removed by distillation. The product was purified by silicagel chromatography to afford the title compound as a colorless oil.

후처리

  1. stirringThe mixture was stirred at ambient temperature for 4 hours
  2. washwashed with water (5 mL), brine (5 mL)
  3. dry with materialdried with MgSO4
  4. customSolvent was removed by distillation
  5. customThe product was purified by silicagel chromatography

출처 및 근거

ORD 기록
ord-4955e9d4488f4c70a01e631513107eb7
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728846

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