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Triethylamine → 8-(trans-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053041
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HRID 2053041 반응식
[OH:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([CH2:8][O:9][CH3:10])[CH:7]=1.[O:16]1[CH:18]2[CH2:19][C:20]3[C:25]([CH:17]12)=[CH:24][CH:23]=[CH:22][CH:21]=3.C(N(CC)CC)C.[Cl-].[NH4+]>CO.O>[OH:16][C@@H:18]1[CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:17]1[O:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([CH2:8][O:9][CH3:10])[CH:7]=1
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 92838Indene oxideHCID 692875158-Hydroxy-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine

생성물 1

HCID 691142778-(trans-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine수율 45%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 962Water용매

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온도
50 °C

실험 절차

To a suspension of 1.0 g (4.9 mmol) 8-hydroxy-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine and 1.3 g (9.7 mmol) 1,2-epoxyindane in 12 ml methanol and 3 ml water are added 1.4 ml triethylamine and the mixture is heated to 50° C. for 24 h. After cooling down, the reaction mixture is poured into 100 ml saturated aqueous ammonium chloride and extracted with dichloromethane. The organic phase is dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using dichloromethane:methanol (20:1) yields 0.7 g (45%) of the title compound as a colourless solid (m.p. 142-143° C.).

후처리

  1. temperatureAfter cooling down
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  4. customevaporated
  5. customPurification of the residue by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-4d04100cd3e3490c9035f70b725cb50f
출처 데이터셋
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07326718B2

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