Guaiacol → HCID 18537920, compound

HRID 505319Notes

Reaction equation

HRID 505319 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1O.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:10][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[O:32][CH3:31])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 18537920HCID 18537920, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of nitrogen, (2-hydroxy-ethyl)-carbamic acid tert-butyl ester (584 mg, 3.62 mmol) and triphenylphosphine (951 mg, 3.63 mmol) were added to a solution of ortho-methoxyphenol (500 mg, 4.03 mmol) in THF (8 ml). Subsequently, diethyl azodicarboxylate (772 mg, 4.44 mmol) was added at 0° C. and the reaction mixture was then stirred for 3 h at r.t. The solvent was evaporated under reduced pressure, the residue was taken up in ethyl acetate, washed (H2O), and dried (Na2SO4). Chromatographic purification gave the title compound (320 mg, 30%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed (H2O)
  3. dry with materialdried (Na2SO4)
  4. customChromatographic purification

Sources & evidence

ORD record
ord-101563d718bb43dbaeb5906140b3234e
Source dataset
uspto-grants-2010_08
Patent number
US07781441B2

Reaction notes

Loading…