Sodium hydride → 1-Cyclopropylidene-6-methoxy-2,3-dihydro-1H-indene

HRID 404322

반응식

HRID 404322 반응식
[H-].[Na+].[Br-].[CH:4]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][CH2:5]1.[CH3:26][O:27][C:28]1[CH:36]=[C:35]2[C:31]([CH2:32][CH2:33][C:34]2=O)=[CH:30][CH:29]=1.COCCOCCN(CCOCCOC)CCOCCOC>C1COCC1>[C:4]1(=[C:34]2[C:35]3[C:31](=[CH:30][CH:29]=[C:28]([O:27][CH3:26])[CH:36]=3)[CH2:32][CH2:33]2)[CH2:6][CH2:5]1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 3340366-Methoxy-1-IndanoneHCID 2723931Cyclopropyltriphenylphosphonium bromide

생성물 1

HCID 574675861-Cyclopropylidene-6-methoxy-2,3-dihydro-1H-indene수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

NaH (1.5 g, 62 mmol) was added to a suspension of cyclopropyltriphenyl-phosphonium bromide (24 g, 62 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) in THF (100 mL), and the resulting mixture was stirred at room temperature for 2 hours. Then, 6-methoxy-1-indanone (H10.1) (Oakwood Products, Inc.) (5.00 g, 31 mmol) and tris(2-(2-methoxyethoxy)ethyl)amine (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (1.1 mL, 3.1 mmol) were added slowly. The resulting mixture was stirred at room temperature for 10 minutes and then at 62° C. for 4 hours. The reaction mixture was concentrated and purified by chromatography (silica gel, eluting with 1:9 EtOAc/hexane) to provide H10.2 (4.53 g, 79% yield) as a solid. MS ESI (pos.) M/E: 187.1 (M+H).

후처리

  1. addition, USA) (1.1 mL, 3.1 mmol) were added slowly
  2. waitat 62° C. for 4 hours
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by chromatography (silica gel, eluting with 1:9 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-9ff4a501133b448da0eb5577c6dd38e4
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748462B2

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