Ammonium Chloride → 1-(2-Bromo-thiazol-5-yl)-propan-1-ol

HRID 1423038Notes

Reaction equation

HRID 1423038 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.[CH2:9]([Mg]Br)[CH3:10].[Cl-].[NH4+]>C1COCC1.C(OCC)C.CCOC(C)=O>[Br:1][C:2]1[S:3][C:4]([CH:7]([OH:8])[CH2:9][CH3:10])=[CH:5][N:6]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 27732592-Bromo-1,3-thiazole-5-carbaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 584433781-(2-Bromo-thiazol-5-yl)-propan-1-ol

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-thiazole-5-carboxaldehyde (1.00 g, 5.21 mmol) in THF (10 mL) is added a 3 M solution of ethylmagnesium bromide (5.00 mL, 15.0 mmol) in diethyl ether. After 18 hours, the reaction is poured into saturated aqueous ammonium chloride (100 mL) containing crushed ice and diluted with EtOAc (100 mL). The organic phase is separated, washed with saturated aqueous sodium bicarbonate solution (100 mL), dried over sodium sulfate, filtered and concentrated. The compound is purified by silica gel chromatography eluting using a gradient of 0-100% EtOAc in hexanes to provide 1-(2-bromo-thiazol-5-yl)-propan-1-ol.

Workup

  1. additioncontaining
  2. customcrushed ice
  3. customThe organic phase is separated
  4. washwashed with saturated aqueous sodium bicarbonate solution (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe compound is purified by silica gel chromatography
  9. washeluting

Sources & evidence

ORD record
ord-e00efad969904fcba1d4e343da2d99e2
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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