Tetrahydrofuran → HCID 23114721, compound

HRID 748746Notes

Reaction equation

HRID 748746 reaction equation
O1CCCC1.Br[C:7]1[S:8][CH:9]=[CH:10][N:11]=1.C([Li])CCC.[F:17][C:18]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:19]=1[CH:20]=[O:21]>CCCCCC>[F:17][C:18]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:19]=1[CH:20]([OH:21])[C:7]1[S:8][CH:9]=[CH:10][N:11]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 764302-BromothiazoleHCID 1376632,5-DifluorobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 23114721HCID 23114721, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran (10 ml) solution of 2-bromothiazole (180 μg, 2 mmol) was added dropwise a hexane solution of n-butyl lithium (1.57M, 1.40 ml, 2.2 mmol) at −78° C. After stirring for 10 minutes, 2,5-difluorobenzaldehyde (238 μl, 2.2 mmol) was added and while stirring, the temperature of the mixture was gradually raised to 0° C. The reaction was then quenched by the addition of an aqueous solution of ammonium chloride, followed by the addition of ether. The ether layer was washed with water and brine, and then, dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1), whereby the title compound (358 mg, 79%) was obtained as an oil.

Workup

  1. stirringwhile stirring
  2. customThe reaction was then quenched by the addition of an aqueous solution of ammonium chloride
  3. additionfollowed by the addition of ether
  4. washThe ether layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1), whereby the title compound (358 mg, 79%)
  9. customwas obtained as an oil

Sources & evidence

ORD record
ord-7172846204f74561af14a103250dad73
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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