Ammonium Chloride → HCID 60204547, compound

HRID 2267414Notes

Reaction equation

HRID 2267414 reaction equation
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[Li]CCCC.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]([C:5]2[S:4][CH:3]=[N:7][CH:6]=2)[OH:21])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 680234-FluorobenzaldehydeHCID 5884532-TrimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 60204547HCID 60204547, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(trimethylsilyl)thiazole (6.12 g, 38.9 mmol) in THF (80 mL) was cooled to −78° C. and treated with a dropwise addition of nBuLi (2.5 M in hexanes, 15.6 mL, 39.0 mmol). The reaction mixture was stirred at −78° C. for 1 h before 4-fluorobenzaldehyde (4.59 mL, 42.8 mmol) was added dropwise. The stirred suspension was allowed to warm gradually to room temperature over 16 h, then treated with 100 mL of saturated aqueous ammonium chloride and 100 mL of EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography, eluting with a gradient of 10-50% EtOAc/hexanes to afford the product as a white solid (4.09 g, 19.5 mmol, 50% yield). MS (M+H)+ 210.

Workup

  1. additionwas added dropwise
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with a gradient of 10-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-3f1a3e9ccaca46309c4c64cf12f27073
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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