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

HRID 1044754Notes

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-].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: -60 °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 (5.00 g, 20.00 mmol) in dry Et2O (40 mL) was added to a n-BuLi (8.40 mL of a 2.5M solution in hexanes, 21.00 mmol) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before DMF (2.5 mL, 32.29 mmol) was added dropwise. The reaction mixture was stirred at −60° C. for 1 h. Sat. aq. NH4Cl (100 mL) was added, followed by aq. 1N HCl (50 mL). The layers separated and the aq. layer extracted with Et2O (5×). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as an orange 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 (5×)
dry with materialextracts were dried over Na2SO4
filtrationfiltered
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-66bfb06d36a440b0961633e147bb23a7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563714B2

Reaction notes

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