1,3-Benzothiazole-2-carbaldehyde → HCID 13444760, compound

HRID 932170Notes

Reaction equation

HRID 932170 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]=[O:11].[CH2:12]([Mg]Br)[CH3:13]>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:11])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 2416081,3-Benzothiazole-2-carbaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 13444760HCID 13444760, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,3-benzothiazole-2-carbaldehyde (0.96 g, 5.88 mmol) in THF (15.0 mL) was added ethylmagnesium bromide (1.0 M solution in THF, 12.0 mL, 12.0 mmol, 2 eq), slowly over 15 minutes (an exotherm was observed). The resulting dark red solution was stirred at room temperature for 55 minutes, then quenched with saturated aqueous ammonium chloride solution (4 mL). The mixture was then concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-70% EtOAc in hexanes gradient) provided the title compound as a red oil.

Workup

  1. customquenched with saturated aqueous ammonium chloride solution (4 mL)
  2. concentrationThe mixture was then concentrated under reduced pressure
  3. customPurification by flash chromatography on silica gel (0-70% EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-9704b400302c443e88a4fd9697342dc2
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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