Boron trifluoride etherate → HCID 11352408, compound

HRID 2106448Notes

Reaction equation

HRID 2106448 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([CH3:15])=[CH:13][C:12]([C:16]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:23]([CH3:35])[CH:22]=3)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:11][C:9]=2[CH:10]=1)=[O:5])C.B(F)(F)F.[CH3:40][CH2:41][O:42]CC>C(O)CO>[C:30]([C:29]1([CH2:28][O:27][C:24]2[CH:25]=[CH:26][C:21]([C:16]([C:12]3[CH:13]=[C:14]([CH3:15])[C:8]4[O:7][C:6]([C:4]([OH:3])=[O:5])=[CH:10][C:9]=4[CH:11]=3)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:22][C:23]=2[CH3:35])[O:34][CH2:40][CH2:41][O:42]1)([CH3:31])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 57810559HCID 57810559, compound

Product 1

HCID 11352408HCID 11352408, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-7-methyl-benzofuran-2-carboxylic acid ethyl ester (506 mg, 1.06 mmol) in ethylene glycol (5.0 mL) is treated with BF3-Et2O (3.0 ml). The reaction mixture is heated to 80° C. and stirred for 3 h. The reaction is quenched with water (20 mL) and extracted with CH2Cl2 (30×2 mL). The organic layer is dried over Na2SO4, concentrated, purified on column chromatography (8% EtOAc/Hex) to afford the title compound (550 mg, 99%).

Workup

  1. customThe reaction is quenched with water (20 mL)
  2. extractionextracted with CH2Cl2 (30×2 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified on column chromatography (8% EtOAc/Hex)

Sources & evidence

ORD record
ord-f4a4e81481bf4a86b5a9e5db60e0532b
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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