Propargyl alcohol → HCID 11571812, compound

HRID 1886029Notes

Reaction equation

HRID 1886029 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH2:7]([OH:10])[C:8]#[CH:9]>C(#N)C.[Cu]I>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[C:9]#[C:8][CH2:7][OH:10]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 764302-Bromothiazole

Product 1

HCID 11571812HCID 11571812, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

Copper (I) iodide (28.5 mg) was added to a stirred solution of 2-bromothiazole (5 g), propargyl alcohol (1.68 g), BTPC (210 mg) and DEA (2.41 g) in acetonitrile (88 ml). The mixture was stirred under nitrogen for 80 h, concentrated and partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was dried and concentrated to yield the crude product which was purified by FCC eluting with toluene/ethyl acetate (5:2) to give the title product as a brown oil (0.68 g), t.l.c. (toluene/ethyl acetate 2:1) Rf 0.27.

Workup

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto yield the crude product which
  6. customwas purified by FCC
  7. washeluting with toluene/ethyl acetate (5:2)

Sources & evidence

ORD record
ord-1fd8f210e2b5451090842380d764cc38
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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