Benzyl Chloride → HCID 70819131, compound

HRID 512093Notes

Reaction equation

[CH2:1]([C:8]1[C:13](=[O:14])[C:12]([I:15])=[C:11]([CH3:16])[NH:10][C:9]=1[CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[H-].[Na+].[H][H].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH2:22]([O:14][C:13]1[C:12]([I:15])=[C:11]([CH3:16])[N:10]=[C:9]([CH3:17])[C:8]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 5 (38 mg, 0.11 mmol) was added to a stirred suspension of oil-free NaH (5 mg, 0.11 mmol) in DMF (5 mL). When evolution of hydrogen ceased, benzyl chloride (14 mg, 0.11 mmol) was added and the mixture was heated at 50° C. for 4 h. The reaction mixture was added to water (5 mL), extracted with portions of ethyl ether. The combined organic phase was dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. Elution with 1:1 hexane/ethyl acetate gave 4-(benzyloxy)-3-heptyl-5-iodo-2,6-dimethylpyridine (19) as a light yellow oil: yield 38 mg (80%); silica gel TLC Rf 0.7 (1:1 hexane/ethyl acetate); 1H NMR (CDCl3) δ 0.61-0.89 (m, 3H), 1.26-1.31 (m, 10H), 2.504 (s, 3H), 2.62-2.65 (m, 2H) 2.75 (s, 3H), 4.95 (s, 2H), 7.38-7.43 (m, 4H) and 7.55-7.57 (m, 1H).

Workup

extractionextracted with portions of ethyl ether
dry with materialThe combined organic phase was dried over anhydrous MgSO4
concentrationconcentrated under diminished pressure
customto afford a crude residue
washElution with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record: ord-188d19f2391047c1a4ce12f933a5886e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102626B2

Reaction notes

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