HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 843169
Notes
Print preview

Reaction equation

HRID 843169 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2adeb33e83304bd38144395ff86093df
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06376491B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes