Dimethylformamide → HCID 23353587, compound

HRID 235107Notes

Reaction equation

[CH2:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[N:8]=1)[CH2:2][CH3:3].C([Li])CCC.CN([CH:25]=[O:26])C>C1COCC1>[CH2:1]([C:4]1[S:5][C:6]([CH:25]=[O:26])=[C:7]([CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[N:8]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2-propyl-4-((2-tetrahydropyranyloxy)methyl)thiazole (12.0 g, 49.8 mmol), from step 548 above, in 120 mL of THF was cooled to -78° C. and treated with n-butyllithium (20.0 mL, 2.5M solution in hexanes). The reaction mixture was stirred at -78° C. for 30 minutes, and 5.46 g (74.7 mmol) of DMF was added. The reaction mixture was stirred at -78° C. for 1.5 hours, then warmed to room temperature and quenched with satd NH4Cl solution. The mixture was partitioned between water and ethyl acetate. The organic extract was washed with water and brine, dried over MgSO4, and concentrated to afford 13.6 g of the title product as a viscous oil, which was taken to the next step without further purification. NMR (CDCl3) δ:10.32 (s, 1H), 5.15 (d, J=12 Hz, 1H), 4.88 (d, J=12 Hz, 1H), 4.81 (t, J=3 Hz, 1H), 3.92-3.82 (m, 1H), 3.61-3.47 (m, 1H), 2.99 (t, J=7 Hz, 2H), 1.9-1.5 (m, 8H), 1.03 (t, J=7 Hz, 3H).

Workup

stirringThe reaction mixture was stirred at -78° C. for 1.5 hours
temperaturewarmed to room temperature
customquenched with satd NH4Cl solution
customThe mixture was partitioned between water and ethyl acetate
extractionThe organic extract
washwas washed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-b37973a21b4a4910977d722924d1d46e
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05597832

Reaction notes

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