Triphenylphosphine → HCID 22009749, compound

HRID 322467Notes

Reaction equation

HRID 322467 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]1[O:19][CH:20]=[C:21]([CH2:23][CH2:24][OH:25])[N:22]=1.O[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][CH2:35][N:36]2[CH:40]=[CH:39][N:38]=[CH:37]2)=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[N:36]1([CH2:35][CH2:34][CH2:33][C:30]2[CH:31]=[CH:32][C:27]([O:25][CH2:24][CH2:23][C:21]3[N:22]=[C:18]([C:14]4[S:13][CH:17]=[CH:16][CH:15]=4)[O:19][CH:20]=3)=[CH:28][CH:29]=2)[CH:40]=[CH:39][N:38]=[CH:37]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22009647HCID 22009647, compoundHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 22009749HCID 22009749, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.20 g) was added dropwise to a stirred mixture of 2-(2-thienyl-4-oxazolyl)ethanol (700 mg). 1-[3-(4-hydroxyphenyl)propyl]imidazole (670 mg), triphenylphosphine (1.73 g), and tetrahydrofuran (50 ml) at room temperature. After refluxing for 3 h, the reaction mixture was concentrated. The residue was purified by silica gel column chromatography. From the fraction eluted with ethyl acetate-methanol (100:1, v/v) 4-[2-[4-[3-(1-imidazolyl)propyl]phenoxy]ethyl]-2-(2-thienyl)oxazole (690 mg, 55%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 77-78° C.

Workup

  1. customat room temperature
  2. temperatureAfter refluxing for 3 h
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was purified by silica gel column chromatography
  5. washFrom the fraction eluted with ethyl acetate-methanol (100:1

Sources & evidence

ORD record
ord-00ba06d57919408c8d5f14e446a345d8
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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