Ethyl ketone → 6-(1-Ethyl-1-hydroxy-propyl)-benzo[b]thiophene-2-carboxylic acid ethyl ester

HRID 730956Notes

Reaction equation

HRID 730956 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12](I)[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2].C([Mg]Br)C.[CH3:20][CH2:21][C:22](=[O:25])[CH2:23][CH3:24]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([C:22]([CH2:23][CH3:24])([OH:25])[CH2:21][CH3:20])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7288Ethyl ketoneHCID 578353956-Iodo-benzo[b]thiophene-2-carboxylic acid ethyl esterHCID 178418443HCID 178418443, compound

Product 1

HCID 578353886-(1-Ethyl-1-hydroxy-propyl)-benzo[b]thiophene-2-carboxylic acid ethyl esterYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-iodo-benzo[b]thiophene-2-carboxylic acid ethyl ester (2.95 g, 8.88 mmol) in THF (60 mL) at −78° C. is added ethylmagnesium bromide (4.45 mL, 3.0 M). The reaction mixture is stirred for 15 min, and 3-pentanone (3.0 mL) is added. The mixture is allowed to warm to RT and stirred for 30 min. The reaction is quenched with HCl (15 mL, 1.0 M) and extracted with EtOAc (2×50 mL). The organic layer is dried over Na2SO4, concentrated, and purified by silica gel column chromatography to give the title compound (0.65 g, 25%).

Workup

  1. stirringstirred for 30 min
  2. customThe reaction is quenched with HCl (15 mL, 1.0 M)
  3. extractionextracted with EtOAc (2×50 mL)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-38f1311829cd433fbfd8a1a3a0083b98
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

Loading…