Guaiacol → HCID 12085651, compound

HRID 747397Notes

Reaction equation

HRID 747397 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]=[CH:9][O:10][C:11]=2[CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1O.C(P(CCCC)CCCC)CCC.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]2[N:8]=[CH:9][O:10][C:11]=2[CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[O:18][CH3:17])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 460GuaiacolHCID 13831TributylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18174738HCID 18174738, compound

Product 1

HCID 12085651HCID 12085651, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(5-chloro-2-thienyl)-5-oxazolebutanol (800 mg), 2-methoxyphenol (770 mg), tributylphosphine (1.24 g) and tetrahydrofuran (10 ml) was added dropwise a toluene solution of diethyl azodicarboxylate (40%, 2.61 g) at room temperature, and the resulting mixture was stirred for 1 hour. After the reaction mixture was concentrated, the residue was subjected to silica gel column chromatography, and 4-(5-chloro-2-thienyl)-5-[4-(2-methoxyphenoxy)butyl]oxazole was obtained as an oil (420 mg, 37%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

Workup

  1. concentrationAfter the reaction mixture was concentrated

Sources & evidence

ORD record
ord-54500562c2d3425c8cb9f9ab713dd2d8
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

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