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Triphenylphosphine → 3-Methyl-4-(piperidin-3-ylmethoxy)-benzofuran-2-carboxylic acid ethyl ester

HRID 843169
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HRID 843169 반응식
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].O[CH2:18][CH:19]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 107308Piperidin-3-ylmethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

생성물 1

HCID 538037073-Methyl-4-(piperidin-3-ylmethoxy)-benzofuran-2-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

A solution of 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (1 g), 3-(hydroxymethyl)piperidine (661 μl), triphenylphosphine (1.55 g) and azodicarboxylic acid diethyl ester (930 μl) in THF (20 ml) was stirred overnight at room temperature. A white precipitate separated out. The precipitate was filtered out and the filtrate was evaporated to dryness. The residue was separated by silica gel column chromatography developed by dichloromethane-methanol to give 3-methyl-4-(piperidin-3-ylmethoxy)-benzofuran-2-carboxylic acid ethyl ester (1.1 g) as a colorless oil. FAB-MS: m/z 318 (MH+); 1H-NMR (CDCl3): δ 1.42-2.02 (4H, m), 1.43 (3H, t, J=7 Hz), 2.43 (1H, m), 2.74 (2H, m), 2.75 (3H, s), 3.34 (1H, br d, J=12 Hz), 3.49 (1H, br d, J=12 Hz), 3.96 (1H, dd, J1=9 Hz, J2=6 Hz), 4.02 (1H, dd, J1=9 Hz, J2=5 Hz), 4.43 (2H, q, J=7 Hz), 6.59 (1H, d, J=8 Hz), 7.13 (1H, d, J=8 Hz), 7.30 (1H, t, J=8 Hz).

후처리

  1. customA white precipitate separated out
  2. filtrationThe precipitate was filtered out
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was separated by silica gel column chromatography

출처 및 근거

ORD 기록
ord-2adeb33e83304bd38144395ff86093df
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06376491B1

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