Acetic Anhydride → (3-Methylthiophen-2-yl)methyl acetate

HRID 2235651Notes

Reaction equation

HRID 2235651 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

HCID 7918Acetic AnhydrideHCID 12875263(3-Methylthiophen-2-yl)methanol

Product 1

HCID 59300595(3-Methylthiophen-2-yl)methyl acetate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

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

  1. washwashed with 1N HCl and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel (0-15% EtOAc/hexane)

Sources & evidence

ORD record
ord-c083b74b5d2a4ba4ada4e6e999eaae8d
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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