Resorcinol, monobenzoate → HCID 54568744, compound

HRID 892193Notes

Reaction equation

HRID 892193 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][OH:11])=[N:7][CH:8]=1)[CH3:2].[C:12]([O:20][C:21]1[CH:27]=[CH:26][CH:25]=[C:23](O)[CH:22]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:26]2[CH:27]=[C:21]([O:20][C:12](=[O:19])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:22]=[CH:23][CH:25]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8690Resorcinol, monobenzoateHCID 11776TriphenylphosphineHCID 788945-Ethyl-2-pyridineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 54568744HCID 54568744, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-ethyl-pyridin-2-yl)-ethanol (480 mg, 3.17 mmol, example 69) in THF (10 mL) is added resorcinol monobenzoate (630 mg, 2.94 mmol), triphenylphosphine (850 mg, 3.24 mmol) and diethyl azodicarboxylate (510 μL, 3.24 mmol). The resulting mixture is stirred for 1 h then concentrated. The residue is purified by flash chromatography (silica, 35% ethyl acetate in hexane) to give the title compound as a yellow oil. MS (ESI) 348 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. customThe residue is purified by flash chromatography (silica, 35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-468afb7d04b54e249bdf1329182c0032
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

Loading…