Chloromethyl Methyl Ether → HCID 67003828, compound

HRID 2362616Notes

Reaction equation

HRID 2362616 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][N:5]=[C:4]1[C:8]1([OH:12])[CH2:11][CH2:10][CH2:9]1.Cl[CH2:14][O:15][CH3:16]>CN(C)C=O>[CH3:14][O:15][CH2:16][O:12][C:8]1([C:4]2[S:3][CH:7]=[CH:6][N:5]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 129928101-(1,3-Thiazol-2-yl)cyclobutan-1-ol

Product 1

HCID 67003828HCID 67003828, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a cold (0° C.) suspension of sodium hydride (1.07 g, 44.4 mmol) in N,N-dimethylformamide (50 mL) was added a solution of 1-(thiazol-2-yl)cyclobutanol (Example 1A) (5.3 g, 34.1 mmol) in N,N-dimethylformamide (18 mL). After 0.5 hours, chloro(methoxy)methane (3.89 ml, 51.2 mmol) was added, and the reaction was stirred for 16 hours. The reaction was quenched by the addition of ether and water. The layers were separated, and the aqueous layer was extracted with additional ether. The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 50% ethyl acetate in hexane, to give the title compound. MS ESI(+) m/z 200 [M+H]+.

Workup

  1. customThe reaction was quenched by the addition of ether and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with additional ether
  4. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with a gradient of 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9504c0b4126b4cb885d12a7bf48cc3dc
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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