HCID 83885318, compound → HCID 118510804, compound

HRID 1053795Notes

Reaction equation

HRID 1053795 reaction equation
[Cl:1][C:2]1[C:3]2[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]=[O:9].[C:14]([Mg]Br)#[CH:15]>C1COCC1>[Cl:1][C:2]1[C:3]2[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]([OH:9])[C:14]#[CH:15]

Participants

4

Reactant 2

HCID 83885318HCID 83885318, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 118510804HCID 118510804, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(3-chlorobenzo[b]thiophen-2-yl)acetaldehyde (1.100 g, 5.60 mmol) in 10 mL THF was added dropwise (cannula) to an ice-cold solution of the ethynylmagnesium bromide (25 mL, 12.5 mmol, 0.5 M/THF). The reaction was stirred for 1 h at 0° C. and for 1 h at room temperature and then was quenched by addition of 100 mL saturated NH4Cl solution. The resulting mixture was extracted with ethyl acetate (3×) and the combined organic solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (475 mg, 65%).

Workup

  1. customwas quenched by addition of 100 mL saturated NH4Cl solution
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×)
  3. dry with materialthe combined organic solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f523ced06906458bbf19bfd3e09bd66f
Source dataset
uspto-grants-2016_07
Patent number
US09394273B2

Reaction notes

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