Water → (4-prop-2-ynylcyclohexyl)methyl Acetate

HRID 1860376Notes

Reaction equation

HRID 1860376 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].N1C=CC=CC=1.[CH2:14]([CH:17]1[CH2:22][CH2:21]C(CO)[CH2:19][CH2:18]1)[C:15]#[CH:16].O>CCOCC>[C:5]([O:4][CH2:1][CH:2]1[CH2:21][CH2:22][CH:17]([CH2:14][C:15]#[CH:16])[CH2:18][CH2:19]1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10796940(4-Prop-2-ynylcyclohexyl)methanol

Product 1

HCID 10726483(4-prop-2-ynylcyclohexyl)methyl AcetateYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acetic anhydride (0.92 mL, 8.25 mmol) and pyridine (0.2 mL, 2.5 mmol) were added to a solution of 5.3 (250 mg, 1.65 mmol) in 25 mL ether. The reaction was allowed to stir at ambient temperature for 24 hours. Water was added to the reaction and the organic was further extracted with 10% NaHCO3. The organic layer was dried with MgSO4 and evaporated. The residue was chromatographed on silica gel with EtOAc-Hexanes (5:95) to yield 5.6 (47%).

Workup

  1. extractionthe organic was further extracted with 10% NaHCO3
  2. dry with materialThe organic layer was dried with MgSO4
  3. customevaporated
  4. customThe residue was chromatographed on silica gel with EtOAc-Hexanes (5:95)

Sources & evidence

ORD record
ord-80aac009d4c745b3b89b0e2f935e2dd9
Source dataset
uspto-grants-2003_03
Patent number
US06531457B2

Reaction notes

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