Monobenzone → HCID 77231474, compound

HRID 491673Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:23]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:18])[CH:24]=2)=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring RT suspension of NaH (0.739 g of a 60% by weight oil dispersion, 18.48 mmol) in DMF (20 mL) was added 4-benzyloxy phenol (3.70 g, 18.48 mmol). The mix was stirred 10 min before cooling to 0° C. and adding 2,4-dichloropyridine (2.734 g, 18.48 mmol). The reaction was warmed to RT. After stirring for 60 h, the reaction was quenched with saturated aqueous NaHCO3 and then basified with 2N NaOH. The crude was extracted twice with Et2O. The organic layers were washed three times with 2 N NaOH, once with brine, then combined and dried over Na2SO4, filtered and dried in vacuo. The crude residue was eluted on a silica gel column with a hexanes/EtOAc system to yield title compound, isolated as the major regioisomer.

Workup

temperatureThe reaction was warmed to RT
stirringAfter stirring for 60 h
customthe reaction was quenched with saturated aqueous NaHCO3
extractionThe crude was extracted twice with Et2O
washThe organic layers were washed three times with 2 N NaOH
dry with materialdried over Na2SO4
filtrationfiltered
customdried in vacuo
washThe crude residue was eluted on a silica gel column with a hexanes/EtOAc system

Sources & evidence

ORD record: ord-5255f584db4649c2a971c2b673e6dd0b
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531553B2

Reaction notes

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