O-Cresol → HCID 57835416, compound

HRID 599680Notes

Reaction equation

HRID 599680 reaction equation
[CH2:1]([C:3]([C:7]1[S:11][C:10]2[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:9]=2[CH:8]=1)(O)[CH2:4][CH3:5])[CH3:2].[C:19]1([CH3:26])[C:24]([OH:25])=[CH:23][CH:22]=[CH:21][CH:20]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([C:3]([C:7]1[S:11][C:10]2[CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=[CH:15][C:9]=2[CH:8]=1)([C:21]1[CH:22]=[CH:23][C:24]([OH:25])=[C:19]([CH3:26])[CH:20]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 335O-CresolHCID 8000Boron trifluoride etherateHCID 57835404HCID 57835404, compound

Product 1

HCID 57835416HCID 57835416, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(1-ethyl-1-hydroxy-propyl)-benzo[b]thiophene-6-carboxylic acid (3.80 g, 14.4 mmol) and o-cresol (1.94 g, 18.0 mmol) in CH2Cl2 (100 mL) at −40° C. is added BF3-Et2O (1.02 g, 7.20 mol). After stirring for 10 min, the reaction mixture is allowed to warm up to 0° C. over 30 min. The reaction is quenched with water (15 mL) and the aqueous layer is extracted with EtOAc (50 mL). The organic layer is dried over Na2SO4, concentrated, and purified by silica gel column chromatography (2% HOAc in 50% EtOAc/Hex) to give the product (3.98 g, 78%).

Workup

  1. customThe reaction is quenched with water (15 mL)
  2. extractionthe aqueous layer is extracted with EtOAc (50 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (2% HOAc in 50% EtOAc/Hex)

Sources & evidence

ORD record
ord-2994bfc040a44e2db05f82e6d7dca807
Source dataset
uspto-grants-2011_03
Patent number
US07897789B2

Reaction notes

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