Acetic Anhydride → (3-Methylthiophen-2-yl)methyl acetate
Reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][OH:8].[C:9](OC(=O)C)(=[O:11])[CH3:10]>N1C=CC=CC=1.CCOC(C)=O>[C:9]([O:8][CH2:7][C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])(=[O:11])[CH3:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 62.2 (0.87 g, 6.79 mmol) in pyridine (20 mL) was added acetic anhydride (0.8 mL, 8.14 mmol) at room temperature. The mixture was stirred overnight at room temperature, diluted with EtOAc, washed with 1N HCl and brine, dried (Na2SO4), and concentrated. The crude product was chromatographed on silica gel (0-15% EtOAc/hexane) to afford 62.3. 1H NMR (400 MHz, CDCl3) δ 7.21 (d, 1H), 6.84 (d, 1H), 5.20 (s, 2H), 2.26 (s, 3H), 2.08 (s, 3H).
Workup
- washwashed with 1N HCl and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude product was chromatographed on silica gel (0-15% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-21810cb283e145759eb80ec1e59c99ea
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003648B2
Reaction notes
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