Nitrogen → 2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

HRID 2064997Notes

Reaction equation

N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:19])([CH3:18])[C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[N:14]=1)([CH3:6])([CH3:5])[CH3:4].COC([O:25][CH3:26])OC.[C:27]([O-])([O-])=O.[Na+].[Na+]>C(O)CO>[C:3]([SiH2:7][O:8][C:9]([CH3:19])([CH3:18])[C:10]1[S:11][CH:12]=[C:13]([C:15]2([CH3:16])[O:25][CH2:26][CH2:27][O:17]2)[N:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-4-yl]-ethanone (1.77 g, 6.52 mmol) in ethylene glycol (7 mL) was treated with trimethylorthoformate (1.46 mL, 13.29 mmol) followed by LiBF4 (125 mg, 1.30 mmol). The reaction mixture was heated at 95° C. for 4 h. Sat. aq. Na2CO3 (5 mL) was added and the mixture was extracted with Et2O (2×20 mL). The org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 3:1 hept-EA) gave the title compound as a brown oil. TLC: rf (1:1 hept-EA)=0.56. LC-MS-conditions 02: tR=1.11 min; [M+H]+=316.36.

Workup

extractionthe mixture was extracted with Et2O (2×20 mL)
dry with materialextracts were dried over Na2SO4
filtrationfiltered
customthe solvent was removed under reduced pressure
customPurification of the residue by FC (20:1 to 3:1 hept-EA)

Sources & evidence

ORD record: ord-1f97db9e0e7f4b5ab7ebcc0af51362a9
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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