Methylparaben → Methyl 4-((5-chloropyridin-3-yl)methoxy)benzoate

HRID 1911142Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.[Cl:26][C:27]1[CH:28]=[C:29]([CH2:33]O)[CH:30]=[N:31][CH:32]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[Cl:26][C:27]1[CH:28]=[C:29]([CH2:33][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=2)[CH:30]=[N:31][CH:32]=1

Participants

Conditions

Temperature: 0 °C

Procedure

DIAD (2.35 mmol, 0.45 mL) was added to an ice-cold solution of methyl 4-hydroxybenzoate 29a (2.35 mmol, 358 mg), (5-chloropyridin-3-yl)methanol 27a (1.57 mmol, 225 mg), and Ph3P (2.35 mmol, 616 mg) in 8 mL of THF. The mixture was stirred at 0° C. for 1 h at room temperature overnight. Water was added and the crude product was purified by flash column chromatography (silica gel, 20% EtOAc/hexanes) to afford 300 mg (68%) of 27b.

Workup

customthe crude product was purified by flash column chromatography (silica gel, 20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-c0e921d2a1234e7fafd6673eeb3bf2e3
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604017B2

Reaction notes

Loading…