Acetic Anhydride → 1-Methylcyclobutyl acetate

HRID 1400764Notes

Reaction equation

HRID 1400764 reaction equation
[CH3:1][C:2]1([OH:6])[CH2:5][CH2:4][CH2:3]1.[C:7](OC(=O)C)(=[O:9])[CH3:8]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:7]([O:6][C:2]1([CH3:1])[CH2:5][CH2:4][CH2:3]1)(=[O:9])[CH3:8]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 1406421-Methylcyclobutanol

Product 1

HCID 133961301-Methylcyclobutyl acetateYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-methylcyclobutanol (6.2 g, 72.0 mmol) in DCM (50 mL) was added DMAP (0.440 g, 3.60 mmol) and TEA (15.05 mL, 108 mmol). Then, the mixture was cooled to 0° C. and acetic anhydride (13.46 mL, 108 mmol) was added and stirred at room temp for 24 h. The mixture was then washed with sat.NaHCO3 (100 mL), 1N HCl (100 mL), 10% NaOH (100 mL), brine (100 mL), dried (Na2SO4), filtered and concentrated to afford 1-methylcyclobutyl acetate (8 g, 62.4 mmol, 87% yield) as light yellow oil which was used in the next step as is without further purification. 1H NMR (500 MHz, CDCl3) δ 2.36-2.26 (m, 2H), 2.18-2.11 (m, 2H), 2.01-1.98 (m, 3H), 1.87-1.76 (m, 1H), 1.72-1.63 (m, 1H), 1.55 (s, 3H).

Workup

  1. washThe mixture was then washed
  2. dry with materialNaHCO3 (100 mL), 1N HCl (100 mL), 10% NaOH (100 mL), brine (100 mL), dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f6014a7bf5e34330b410728567ba6040
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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