Triphenylphosphine → HCID 23024764, compound

HRID 350045Notes

Reaction equation

HRID 350045 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.[S:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[CH2:44]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C1(C)C=CC=CC=1>[S:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[CH2:44][O: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

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 694672-ThiophenemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23024736Ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate

Product 1

HCID 23024764HCID 23024764, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A toluene solution (1.74 g) of 40% diethyl azodicarboxylate was added dropwise slowly to a mixture of ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (873 mg), 2-thiophenemethanol (0.237 ml), triphenyl phosphine (984 mg), and tetrahydrofuran (20 ml) at room temperature. After the solution was stirred overnight at room temperature, the reaction solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography, and ethyl 3-[1-[4-(2-thienylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate (620 mg, yield: 56%) 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-f8e55ca4b8c341ae8e3eb4e0ffe3af54
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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