Acetic Anhydride → Ethyl acetate hexane

HRID 1881379Notes

Reaction equation

HRID 1881379 reaction equation
[CH3:1][C@:2]1(O)[CH2:6][C@@H:5](O)[CH:4]=[CH:3]1.[C:9]([O:12][C:13](=O)[CH3:14])(=[O:11])[CH3:10]>C1COCC1.CN(C1C=CN=CC=1)C>[C:9]([O:12][CH2:13][CH3:14])(=[O:11])[CH3:10].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 121518744-Cyclopentene-1,3-diol, 1-methyl-, (1S,3R)-

Product 1

HCID 21226206Ethyl acetate hexaneYield 58.77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9 (100 mg, 0.877 mmol) in dry THF (10 ml) at room temperature was added acetic anhydride (89 mg, 0.877 mmol), and catalytic amount of DMAP. The reaction was allowed to stir for 3 h and then concentrated. The residue was taken in ethyl acetate (40 ml) and was treated twice with saturated sodium bicarbonate solution (20 ml), followed by brine (10 ml). The organic layer was dried over sodium sulfate and the resulting product 13 was purified by column chromatography using ethyl acetate/hexane (1:2) (80.25 mg, yield=58.77%).

Workup

  1. concentrationconcentrated
  2. additionwas treated twice with saturated sodium bicarbonate solution (20 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe resulting product 13 was purified by column chromatography

Sources & evidence

ORD record
ord-e3c23bef7b314636885bf2f97edd8f80
Source dataset
uspto-grants-2012_11
Patent number
US08318804B2

Reaction notes

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