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

HRID 2040028Notes

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-cbba2ff253e7416fa0205333a9ed624d
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580831B2

Reaction notes

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