O-Cresol → HCID 57810551, compound

HRID 2106426Notes

Reaction equation

HRID 2106426 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([CH2:17][CH3:18])(O)[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:19]=1)=[O:4].[C:20]1([CH3:27])[C:25]([OH:26])=[CH:24][CH:23]=CC=1.B(F)(F)F.[CH3:32][CH2:33]OCC>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([CH2:32][CH3:33])([C:17]3[CH:23]=[CH:24][C:25]([OH:26])=[C:20]([CH3:27])[CH:18]=3)[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:19]=1)=[O:4]

Participants

5

Reactant 3

HCID 335O-CresolHCID 8000Boron trifluoride etherateHCID 57810594HCID 57810594, compound

Product 1

HCID 57810551HCID 57810551, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-(1-ethyl-1-hydroxy-propyl)-benzofuran-5-carboxylic acid methyl ester (6.01 g, 22.9 mmol) and o-cresol (3.71 g, 34.4 mmol) in CH2Cl2 (150 mL) at −78° C. is added BF3-Et2O (1.63 ml, 11.5 mol). After stirring for 5 min, the reaction mixture is allowed to warm up to 0° C. over 30 min. The reaction is quenched with water (50 mL) and extracted with CH2Cl2 (50 mL). The organic layer is dried over Na2SO4, concentrated, purified on column chromatography (15-20% EtOAc/Hex) to afford the title compound (7.38 g, 91%).

Workup

  1. customThe reaction is quenched with water (50 mL)
  2. extractionextracted with CH2Cl2 (50 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified on column chromatography (15-20% EtOAc/Hex)

Sources & evidence

ORD record
ord-5c90ec54c5b44d88adc24d591789c268
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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