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

HRID 1668286Notes

Reaction equation

HRID 1668286 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>CN(C=O)C>[C:18]([O:11][CH2:10][CH:7]1[CH2:8][CH2:9][CH:4]([CH2:1][C:2]#[CH:3])[CH2:5][CH2:6]1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

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

Product 1

HCID 10726483(4-prop-2-ynylcyclohexyl)methyl AcetateYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 960 mg (6.31 mmol) of 86 in 6 mL DMF was added 0.62 mL (7.57 mmol) pyridine and 0.78 mL (8.27 mmol) acetic anhydride. The reaction was allowed to stir overnight at room temperature. After 16 hours, starting material still remained. The reaction mixture was heated at 75° C. for 3 hours. The solvent was removed under reduced pressure to yield a yellow oil which was purified by flash chromatography, on silica gel, eluting with 1:3 ether/petroleum ether to yield 1.12 g (91%) of 87 as an oil. 1H NMR (CDCl3) δ3.87 (d, J=6.2 Hz, 2H), 2.06 (d, J=4.3 Hz, 2H), 2.03 (s, 3H), 1.98-1.93 (m, 1H), 1.92-1.83 (m, 2H), 1.83-1.74 (m, 2H), 1.63-1.36 (m, 2H), 1.12-0.90 (m, 4H); 13C NMR (CDCl3) δ 171.7, 83.7, 69.9, 69.6, 37.4, 37.3, 32.1, 29.7, 26.5, 21.4; APCI m/z (rel intensity) 195 (M+, 30), 153 (M+, 70), 135 (M+, 100).

Workup

  1. waitAfter 16 hours
  2. temperatureThe reaction mixture was heated at 75° C. for 3 hours
  3. customThe solvent was removed under reduced pressure
  4. customto yield a yellow oil which
  5. customwas purified by flash chromatography, on silica gel
  6. washeluting with 1:3 ether/petroleum ether

Sources & evidence

ORD record
ord-3ab14c3c8f0747a1963d72b118515d20
Source dataset
uspto-grants-2011_08
Patent number
US07989431B2

Reaction notes

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