Potassium Carbonate → 5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole

HRID 1881866Notes

Reaction equation

HRID 1881866 reaction equation
Cl[C:2]1[S:3][C:4]([CH2:7][O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+]>[C].[Pd].CO>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[O:8][CH2:7][C:4]1[S:3][CH:2]=[N:6][CH:5]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 684330372-chloro-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole

Product 1

HCID 179531985-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazoleYield 79%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole (10.4 g), 10% palladium carbon (containing 50% water, 2.0 g), potassium carbonate (6.2 g) and methanol (10 mL) was stirred under hydrogen atmosphere (5 atm) at 60° C. for 10 hr. The insoluble material was filtered off, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (6.97 g, yield 79%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e57ea491e2944329bda71f7be1763a4f
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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