Acetic Acid → HCID 57472889, compound

HRID 1754031Notes

Reaction equation

HRID 1754031 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]#[C:13][Si](C)(C)C)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CC(O)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOCC>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][C:12]#[CH:13])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 68286487HCID 68286487, compound

Product 1

HCID 57472889HCID 57472889, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7 (5.37 g, 21.6 mmol, 1 equiv) was dissolved in THF (100 mL) and AcOH (4.99 mL, 86.5 mmol, 4 equiv) was added followed by dropwise addition of TBAF (1 M in THF; 86.5 mL, 86.5 mmol, 4 equiv). The resulting reaction was allowed to stir at room temperature for 24 h. The reaction was diluted with Et2O, washed with brine (×2), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude mixture was purified by chromatography on SiO2 (EtOAc/hexanes, 1:10) to give 3.85 g (100% yield) of the desired product as a colorless oil: Rf 0.36 (EtOAc/hexanes, 1:10); IR (CDCl3) 3286, 2999, 2954, 1593, 1457, 1428, 1344, 1323, 1288, 1204, 1154, 1064, 827; 1H NMR (400 MHz, CDCl3) δ 6.53 (d, 2 H, J=2.4 Hz), 6.35 (t, 1 H, J=2.4 Hz), 3.79 (s, 6 H), 3.56 (d, 2 H, J=2.8 Hz), 2.20 (t, 1H, J=2.8 Hz); 13C NMR (100 MHz, CDCl3) δ 160.9, 138.3, 105.9, 98.7, 81.7, 70.6, 55.3, 25.0; HRMS (EI+) m/z calcd for C11H12O2 176.0837, found 176.0834.

Workup

  1. customThe resulting reaction
  2. washwashed with brine (×2)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified by chromatography on SiO2 (EtOAc/hexanes, 1:10)

Sources & evidence

ORD record
ord-c5a5fcecb672492fa5c778120ce84786
Source dataset
uspto-grants-2015_10
Patent number
US09169182B2

Reaction notes

Loading…