Nitrogen → (2-(Methoxymethyl)thiazol-5-yl)methanol

HRID 82830Notes

Reaction equation

HRID 82830 reaction equation
N#N.[Si]([O:10][CH2:11][C:12]1[S:16][C:15]([CH2:17][O:18][CH3:19])=[N:14][CH:13]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(=O)OCC>[CH3:19][O:18][CH2:17][C:15]1[S:16][C:12]([CH2:11][OH:10])=[CH:13][N:14]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 2724141Tetrabutylammonium FluorideHCID 866982065-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-2-(methoxymethyl)thiazole

Product 1

HCID 64980908(2-(Methoxymethyl)thiazol-5-yl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(methoxymethyl)thiazole (721 mg, 2.64 mmol) in THF (20 mL) was treated at 0° C. with TBAF (5.30 mL of a 1M solution in THF, 5.30 mmol) and the resulting mixture was stirred for 45 min at 0° C. The reaction mixture was diluted with EA, washed with sat. aq. NH4Cl and brine, dried over Na2SO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (1:9 hept-EA) gave the title compound as a colorless oil: TLC: rf (1:9 hept-EA)=0.27. LC-MS-conditions 07: tR=0.41 min, [M+H]+=160.01.

Workup

  1. washwashed with sat. aq. NH4Cl and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (1:9 hept-EA)

Sources & evidence

ORD record
ord-46d02a1dee8e4f369dfdb16fb9e08382
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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