Nitrogen → [2-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-5-yl]-methanol

Temperature

95 °C

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-thiazol-2-yl]-ethanone (1.00 g, 3.68 mmol) in ethylene glycol (4 mL) was treated with trimethylorthoformate (0.82 mL, 7.51 mmol) followed by LiBF4 (70 mg, 0.74 mmol). The reaction mixture was heated at 95° C. for 2 days. Sat. aq. Na2CO3 (5 mL) was added and the mixture was extracted with Et2O (3×20 mL). The org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. The crude residue (mixture of silylated/desilylated products) in dry THF (10 mL) was treated at rt with TBAF (1.1 mL of a 1M solution in THF, 1.10 mmol). The reaction mixture was stirred at rt until completion of the reaction. The mixture was then diluted with EA, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (4:1->1:2 hept-EA) gave the title compound as a pale yellow solid. TLC: rf (EA)=0.47. LC-MS-conditions 02: tR=0.60 min; [M+H]+=202.46.

1. extractionthe mixture was extracted with Et2O (3×20 mL)
2. dry with materialextracts were dried over Na2SO4
3. filtrationfiltered
4. customthe solvent was removed under reduced pressure
5. additionThe crude residue (mixture of silylated/desilylated products) in dry THF (10 mL) was treated at rt with TBAF (1.1 mL of a 1M solution in THF, 1.10 mmol)
6. additionThe mixture was then diluted with EA
7. washwashed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customPurification of the residue by FC (4:1->1:2 hept-EA)

ORD record

ord-ea5badc077ad49a091f790e96f1b06bc

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563714B2