Benzyl Alcohol → HCID 86690770, compound

HRID 1471729Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of NaH (60% in mineral oil) (2.77 g, 69.25 mmol, 2.5 eq.) in DMF (40.0 mL) was added benzyl alcohol (6.6 g, 61.0 mmol, 12 eq.) at 0° C. The mixture was stirred at 0° C. for 10 min, added 3,5-dichloroisonicotinonitrile (4.8 g, 27.7 mmol, 1 eq.), continued to stir at 0° C. for 30 min, gradually warm to rt, stirred at rt O/N, and quenched with NH4Cl(sat.) solution. The aqueous layer was extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 3,5-bis(benzyloxy)isonicotinonitrile (4.94 g, 56%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 2H), 7.58-7.30 (m, 10H), 5.33 (s, 4H). LRMS (M+H+) m/z 317.1

Workup

stirringto stir at 0° C. for 30 min
temperaturegradually warm to rt
stirringstirred at rt O/N
customquenched with NH4Cl(sat.) solution
extractionThe aqueous layer was extracted with EtOAc three times
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
custompurified on silica gel using
additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record: ord-a78afdefc18c4257928745f1dd815a55
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012450B2

Reaction notes

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