Dodecanoyl chloride → HCID 15037161, compound

HRID 2081341Notes

Reaction equation

HRID 2081341 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]=1[CH2:7][OH:8].C(N(CC)CC)C.[C:22](Cl)(=[O:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>O1CCCC1>[C:22]([O:8][CH2:7][C:6]1[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][O:3][C:2]=1[CH3:1])(=[O:34])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 15037160HCID 15037160, compound2×

Product 1

HCID 15037161HCID 15037161, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-methyl-4-phenyl-3-furanmethanol (Compound 59, 48 mg, 0.26 mmol) and triethylamine (39 mg. 0.38 mmol) in tetrahydrofuran (3 ml) at 0 degrees under argon was added lauroyl chloride (73 mg. 0.33 mmol). This solution was warmed gradually to room temperature and stirred for 4 1/2 hours. The organics were extracted into ethyl ether and washed with a 5% aqueous sodium bicarbonate solution, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 3% ether/hexanes to give the title compound.

Workup

  1. extractionThe organics were extracted into ethyl ether
  2. washwashed with a 5% aqueous sodium bicarbonate solution, H2O and brine
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil which
  6. customwas purified by flash chromatography on silica using 3% ether/hexanes

Sources & evidence

ORD record
ord-f9e43e609b9d41c9b7d7f776d63e1748
Source dataset
uspto-grants-1993_02
Patent number
US05183906

Reaction notes

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