O-Cresol → HCID 57835400, compound

HRID 599673Notes

Reaction equation

HRID 599673 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([C:15]([CH2:19][CH3:20])(O)[CH2:16][CH3:17])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2].[C:21]1([CH3:28])[C:26]([OH:27])=[CH:25][CH:24]=[CH:23][CH:22]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([C:15]([CH2:16][CH3:17])([C:23]3[CH:24]=[CH:25][C:26]([OH:27])=[C:21]([CH3:28])[CH:22]=3)[CH2:19][CH3:20])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 335O-CresolHCID 8000Boron trifluoride etherateHCID 578353886-(1-Ethyl-1-hydroxy-propyl)-benzo[b]thiophene-2-carboxylic acid ethyl ester

Product 1

HCID 57835400HCID 57835400, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 6-(1-ethyl-1-hydroxy-propyl)-benzo[b]thiophene-2-carboxylic acid ethyl ester (0.650 g, 2.23 mmol and o-cresol (0.480 g, 4.45 mmol) in CH2Cl2 (20 mL) at −78° C. is added BF3-Et2O (0.316 g, 2.23 mol). After stirring for 10 min, the reaction mixture is allowed to warm to 0° C. over 30 min. The reaction is quenched with water (15 mL) 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 (0.780 g, 92%).

Workup

  1. customThe reaction is quenched with water (15 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-eb4ddd1739a745308038402d729c1bb6
Source dataset
uspto-grants-2011_03
Patent number
US07897789B2

Reaction notes

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