4-Chlorophenol → HCID 53721700, compound

HRID 1383466Notes

Reaction equation

HRID 1383466 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[NH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:1]([O:8][C:9](=[O:17])[NH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][C:22]1[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11064482benzyl 2-(2-hydroxyethoxy)ethylcarbaMate

Product 1

HCID 53721700HCID 53721700, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid benzyl ester (2.39 g, 10 mmol), 4-chlorophenol (1.29 g, 10 mmol), and triphenylphosphine (2.89 g, 11 mmol) were dissolved in tetrahydrofuran (50 ml), followed by the dropwise addition of diethylazodicarboxylate (1.73 ml, 11 mmol). After the addition, the reaction solution was stirred at room temperature for 10-12 hours. The solvent was then removed in vacuo. The remaining residue was stirred in 30% EtOAc in hexane (200 mL) for 10 minutes and a white solid was formed. This solid was then filtered and washed with 30% EtOAc in hexane (3×20 mL). The filtrates were combined and the solvents were removed in vacuo. The remaining residue was purified by flash column chromatography (SiO2, 2:1 hexane:EtOAc) to give {2-[2-(4-chloro-phenoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester as clear solid (3.49 g, 99.8% yield). 1H-NMR (CDCl3, ppm) 7.35 (m, 5H), 7.20 (d, 2H), 6.82 (d, 2H), 5.22 (b, 1H), 5.10 (s, 2H), 4.07 (t, 2H), 3.80 (t, 2H), 3.62 (t, 2H), 3.41 (q, 2H). ESMS 350.1 (M+l), 372.1 (M+23).

Workup

  1. additionAfter the addition
  2. customThe solvent was then removed in vacuo
  3. stirringThe remaining residue was stirred in 30% EtOAc in hexane (200 mL) for 10 minutes
  4. customa white solid was formed
  5. filtrationThis solid was then filtered
  6. washwashed with 30% EtOAc in hexane (3×20 mL)
  7. customthe solvents were removed in vacuo
  8. customThe remaining residue was purified by flash column chromatography (SiO2, 2:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-1ada3b87eb2c4f33b97d361299f1e628
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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