Nitrogen → 5-(2-Methyl-[1,3]dioxolan-2-yl)-thiazole-2-carbaldehyde

HRID 2065046Notes

Reaction equation

N#N.Br[C:4]1[S:5][C:6]([C:9]2([CH3:14])[O:13][CH2:12][CH2:11][O:10]2)=[CH:7][N:8]=1.[Li]CCCC.CN([CH:23]=[O:24])C.[NH4+].[Cl-]>CCOCC>[CH3:14][C:9]1([C:6]2[S:5][C:4]([CH:23]=[O:24])=[N:8][CH:7]=2)[O:13][CH2:12][CH2:11][O:10]1

Participants

Conditions

Temperature: -20 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole (780 mg, 3.12 mmol) in dry Et2O (10 mL) was added to a n-BuLi (1.25 mL of a 2.5M solution in hexanes, 3.13 mmol) solution in Et2O (10 mL) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before DMF (0.29 mL, 3.78 mmol) was added dropwise. The reaction mixture was allowed to warm up to −20° C. and stirred at this temperature for 20 min. Sat. aq. NH4Cl (10 mL) was added, the layers separated and the aq. layer extracted with Et2O (3×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (10:1 to 3:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (1:1 hept-EA)=0.50. LC-MS-conditions 01: tR=0.78 min, [M+H]+=199.93.

Workup

additionwas added dropwise
customthe layers separated
extractionthe aq. layer extracted with Et2O (3×10 mL)
dry with materialextracts were dried over Na2SO4
filtrationfiltered
customthe solvent was removed under reduced pressure
customPurification of the residue by FC (10:1 to 3:1 hept-EA)

Sources & evidence

ORD record: ord-a9c1820cc7194df3ace3eec51475b027
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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