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

HRID 2067987Notes

Reaction equation

HRID 2067987 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)(=O)C>[Br:1][C:2]1[S:3][C:4]([CH:7]([OH:8])[CH2:9][CH3:10])=[CH:5][N:6]=1

Participants

6

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-olYield 42%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-thiazole-5-carbaldehyde (1.00 g, 5.21 mmol) was dissolved in THF (10 ml). A solution of ethylmagnesium bromide (3 M in diethylether, 5.00 mL, 15.0 mmol) was added. The mixture was stirred for 18 h. The reaction was poured into sat. ammonium chloride solution/ice (100 mL) and diluted with ethyl acetate (100 ml). The organic phase was separated, washed with sodium bicarbonate solution (100 mL), dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes provided 1-(2-bromo-thiazol-5-yl)-propan-1-ol (480 mg, 42%). Unreacted 2-Bromo-thiazole-5-carbaldehyde (465 mg, 46%) was also obtained.

Workup

  1. customThe organic phase was separated
  2. washwashed with sodium bicarbonate solution (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography
  7. washeluting with a gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a0e026cb08ac44dd908857dca64d452a
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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