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

HRID 42770Notes

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->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->3:1 hept-EA)

Sources & evidence

ORD record: ord-69f08f4cba7b4fed8bb7d3ec6829d17b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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