Potassium Carbonate → HCID 25140254, compound

HRID 2272768Notes

Reaction equation

HRID 2272768 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[CH:13][C:12]=1[OH:21].I[CH2:23][CH2:24][CH3:25]>CN(C)C=O>[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][O:19][CH3:20])[CH:14]=[CH:13][C:12]=1[O:21][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 11042104HCID 11042104, compound

Product 1

HCID 25140254HCID 25140254, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (322 mg, 2.33 mmol) was added to 3b (50 mg, 0.233 mmol) in N,N-dimethylformamide (2.33 mL) at room temperature. After 10 minutes, iodopropane (226 μL, 2.33 mmol) was added and the solution was heated to reflux for 12 hours. Upon cooling to room temperature, the solution was extracted with EtOAc (3×10 mL); combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (SiO2, 5:1 Hexane:EtOAc) to afford 4b as a yellow oil (36.4 mg, 61%): 1H NMR (CD2Cl2, 400 MHz) δ 6.87 (s, 1H), 6.84 (d, J=2.9 Hz, 1H), 6.68 (dd, J=11.7, 2.8 Hz, 1H), 5.19 (s, 2H), 5.12 (s, 2H), 3.93 (t, J=6.6 Hz, 2H), 3.53 (s, 3H), 3.49 (s, 3H), 1.86-1.78 (m, 2H), 1.06 (t, J=7.5 Hz, 3H); 13C NMR (CDCl3, 125 MHz) δ 150.6, 146.5, 143.8, 113.7, 108.5, 106.6, 94.7, 94.2, 70.3, 55.2, 54.9, 21.6, 9.5; IR (film) νmax 2961, 2826, 1595, 1506, 1400, 1261, 1154, 1013, 1076, 924, 800 cm−1; HRMS (ESI+) m/z: [M+H]+ calcd for C13H20O5, 257.1389. found, 257.1410; [M Na]+ calcd for C13H20O5, 279.1208. found, 279.1165.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 12 hours
  3. extractionthe solution was extracted with EtOAc (3×10 mL)
  4. washcombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (SiO2, 5:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-cfb53fe00c324d9bba2dd16819a54004
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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