Boron trifluoride etherate → HCID 57835408, compound

HRID 730992Notes

Reaction equation

HRID 730992 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([C:15]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:34])[CH:21]=3)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2].B(F)(F)F.[CH3:39][CH2:40][O:41]CC>C(O)CO>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([C:15]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4([C:29]([CH3:31])([CH3:30])[CH3:32])[O:41][CH2:40][CH2:39][O:33]4)=[C:22]([CH3:34])[CH:21]=3)([CH2:16][CH3:17])[CH2:18][CH3:19])=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 57835396HCID 57835396, compound

Product 1

HCID 57835408HCID 57835408, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzo[b]thiophene-2-carboxylic acid ethyl ester (170 mg, 0.354 mmol)) in ethylene glycol (3.0 mL) is treated with BF3-Et2O (2.0 mL). The mixture is stirred at 90° C. for 6 h, cooled to RT, and quenched with water (50 mL). The mixture is extracted with EtOAc (2×20 mL), and the organic layer is concentrated and purified using silica gel column chromatography (10% EtOAc/Hex) to afford the product as an oil (94 mg, 51%).

Workup

  1. temperaturecooled to RT
  2. customquenched with water (50 mL)
  3. extractionThe mixture is extracted with EtOAc (2×20 mL)
  4. concentrationthe organic layer is concentrated
  5. custompurified

Sources & evidence

ORD record
ord-f0153cfe24fa4dc8b519c026a5b1421f
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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