Triethylamine → HCID 46897090, compound

HRID 1928676Notes

Reaction equation

HRID 1928676 reaction equation
[CH3:1][C:2]1[O:8][CH:7]=[C:6]([OH:9])[C:4](=[O:5])[CH:3]=1.C(N(CC)CC)C.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22](Cl)=[O:23]>C1COCC1>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([O:9][C:6]1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[O:8][CH:7]=1)=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 695214H-Pyran-4-one, 5-hydroxy-2-methyl-

Product 1

HCID 46897090HCID 46897090, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Allomaltol (1.256 g, 10 mmol) was dissolved in 40 mL of anhydrous THF. The mixture was cooled to 0° C. Triethylamine (1.8 mL, 13 mmol) was added. Furan-2-carbonyl chloride (1.500 g, 11 mmol) was added dropwise. Cold bath was removed and the mixture was stirred at room temperature overnight. The reaction was extracted with EtOAc. The organic phase was washed with brine 2 times then dried over Na2SO4 and concentrated. The crude product was purified with flash chromatography using EtOAc/hexanes to give the desired product as a brown solid (1.539 g, 70%). MP (136° C.). 1H NMR (CDCl3) δ (ppm): 2.30 (s, 3H), 6.29 (s, 1H), 6.55 (m, 1H), 7.37 (m, 1H), 7.64 (m, 1H), 7.94, (s, 1H). 13C NMR (CDCl3) δ (ppm): 19.8, 112.6, 115.4, 120.8, 140.5, 143.0, 147.9, 148.4, 155.4, 166.5, 172.1.

Workup

  1. customCold bath was removed
  2. extractionThe reaction was extracted with EtOAc
  3. washThe organic phase was washed with brine 2 times
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified with flash chromatography

Sources & evidence

ORD record
ord-02586c3ac31242829cb40382c1a27c03
Source dataset
uspto-grants-2012_05
Patent number
US08183398B2

Reaction notes

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