Triphenylphosphine → Ethyl 3-[1-[4-(3-furylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate

HRID 350044

Reaction equation

HRID 350044 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:38]=[CH:37][C:17]([CH2:18][N:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:20]2)=[CH:16][CH:15]=1.[O:39]1[CH:43]=[CH:42][C:41]([CH2:44]O)=[CH:40]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C1(C)C=CC=CC=1>[O:39]1[CH:43]=[CH:42][C:41]([CH2:44][O:13][C:14]2[CH:38]=[CH:37][C:17]([CH2:18][N:19]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:21]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:20]3)=[CH:16][CH:15]=2)=[CH:40]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 204493-FuranmethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23024736Ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate

Product 1

HCID 69420280Ethyl 3-[1-[4-(3-furylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionateYield 45%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A toluene solution (1.04 g) of 40% diethyl azodicarboxylate was added dropwise slowly to a mixture of ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (699 mg), 3-furanmethanol (0.172 ml), triphenylphosphine (577 mg) and tetrahydrofuran (20 ml) at room temperature. After the solution was stirred at room temperature overnight, the reaction solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography, and ethyl 3-[1-[4-(3-furylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate (385 mg, yield: 45%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

  1. customthe reaction solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d4a4522621f64fc68aa4c3738d0a2228
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Linked notes

Loading…