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

HRID 1375264

반응식

HRID 1375264 반응식
CC1[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])(C)[CH2:9][CH:8]=2)=CC=1.[Li][C:21](C)(C)[CH3:22].[CH3:25]CCCC.CN([CH:33]=[O:34])C.C(=O)=O.[CH2:38]1[CH2:42]O[CH2:40][CH2:39]1>CCOCC>[CH3:40][C:39]1[S:6][C:5]([C:7]2[C:16]3[C:11](=[CH:10][CH:19]=[C:25]([CH:33]=[O:34])[CH:15]=3)[C:12]([CH2:13][CH3:14])([CH2:21][CH3:22])[CH2:9][CH:8]=2)=[CH:42][CH:38]=1

참가 물질

8

반응물 6

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 8003PentaneHCID 8028TetrahydrofuranHCID 186200621-(5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene2회HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 210795151(5-Methyl-thien-2-yl)3,4-dihydro-4,4-diethyl-7-naphthaldehyde

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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-0dfef76ef84349f897b21b46838ad55b
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166726B2

연결된 노트

불러오는 중…