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Tetrabutylammonium Fluoride → Methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate

HRID 1481711
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HRID 1481711 반응식
[Si]([O:8][CH2:9][C:10]1[N:14]([CH3:15])[C:13]2[S:16][C:17]([C:19]3[C:28]([CH2:29][CH3:30])=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([O:31][CH3:32])[N:20]=3)=[CH:18][C:12]=2[CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:29]([C:28]1[C:19]([C:17]2[S:16][C:13]3[N:14]([CH3:15])[C:10]([CH2:9][OH:8])=[CH:11][C:12]=3[CH:18]=2)=[N:20][C:21]([O:31][CH3:32])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])[CH3:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 71281709Methyl 6-(5-((tert-butyldimethylsilyloxy)methyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-5-ethyl-2-methoxynicotinate

생성물 1

HCID 71281796Methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate수율 51.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To solution of methyl 6-(5-((tert-butyldimethylsilyloxy)methyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-5-ethyl-2-methoxynicotinate (0.594 g, 1.25 mmol) in THF (8 mL) was added solution of TBAF (1M THF, 1.50 mL, 1.50 mmol). Reaction mixture was stirred at room temperature for 30 min and THF was then concentrated. Residue was loaded directly on the column and product was isolated eluting with EtOAc/hexanes gradient (0-50%). Methyl 5-ethyl-6-(5-(hydroxymethyl)-6-methyl-6H-thieno[2,3-b]pyrrol-2-yl)-2-methoxynicotinate (0.233 g, 26% 2 steps) was obtained as solid.

후처리

  1. customReaction mixture
  2. concentrationTHF was then concentrated
  3. customproduct was isolated
  4. washeluting with EtOAc/hexanes gradient (0-50%)

출처 및 근거

ORD 기록
ord-060719690091471ab5641fc461a53176
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409905B2

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