Sodium hydride → HCID 66783731, compound

HRID 1096819Notes

Reaction equation

HRID 1096819 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][OH:9].[CH3:10][O:11][C:12](=[O:15])[CH2:13]Br>C1COCC1>[CH3:10][O:11][C:12](=[O:15])[CH2:13][O:9][CH2:8][C:4]1[S:3][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 27952131,3-Thiazol-2-ylmethanol

Product 1

HCID 66783731HCID 66783731, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

NaH (55% dispersion in oil, 1.4 g) was added to a stirred sol. of thiazol-2-ylmethanol (3.55 g, 30.8 mmol) in THF (155 mL). The suspension was then heated to 45° C. for 1 h, and methylbromoacetate (3.40 mL, 37.0 mmol) was added. Stirring was continued at 45° C. for 4 h. The reaction mixture was partitioned between EtOAc and H2O, the phases separated, and the aq. layer extracted with EtOAc (2×). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed in vacuo. Purification of the crude by FC (MeOH/CH2Cl2 1:9) yielded the title compound (5.50 g, 95%) as an orange oil. LC-MS: tR=0.62 min, ES+: 188.14.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and H2O
  2. customthe phases separated
  3. extractionthe aq. layer extracted with EtOAc (2×)
  4. dry with materiallayers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed in vacuo
  7. customPurification of the crude by FC (MeOH/CH2Cl2 1:9)

Sources & evidence

ORD record
ord-46b0d78588654c93a91174c43445e52a
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

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