Ethyl Acetate → HCID 23391440, compound

HRID 523620Notes

Reaction equation

HRID 523620 reaction equation
[C:1]([O:6][CH2:7][CH2:8][S:9]([CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])(=[O:11])=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].COC1C=CC(O)=CC=1.CCOC(C)=O>C(O)(C(F)(F)F)=O>[C:1]([O:6][CH2:7][CH2:8][S:9]([CH2:12][C:13]([OH:15])=[O:14])(=[O:11])=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 90154-MethoxyphenolHCID 86697509HCID 86697509, compound

Product 1

HCID 23391440HCID 23391440, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
55 °C

Procedure

Pure 7 (1.2 g, 3.9 mmol) was dissolved in TFA (15 mL) under nitrogen. A trace amount of MEHQ was added to the mixture and the reaction was stirred for 3 hours at 55° C. Completion of the reaction was confirmed by TLC (EtOAc/Hex/TFA: 60:40:0.1% (v/v), Rf: 0.38). The reaction mixture was purified on a silica gel column (EtOAc/Hex, 3/2). 0.6 g (65% yield) 8 was obtained as yellow oil.

Workup

  1. customThe reaction mixture was purified on a silica gel column (EtOAc/Hex, 3/2)

Sources & evidence

ORD record
ord-7b2fdf0deb1a443ab5a67757de716479
Source dataset
uspto-grants-2016_05
Patent number
US09339554B2

Reaction notes

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