Acetic Anhydride → HCID 19385052, compound

HRID 2399909Notes

Reaction equation

HRID 2399909 reaction equation
[OH:1][CH:2]([C:15]1[CH:19]([CH3:20])[O:18][C:17](=[O:21])[CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:22](OC(=O)C)(=[O:24])[CH3:23].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1>[C:22]([O:1][CH:2]([C:15]1[CH:19]([CH3:20])[O:18][C:17](=[O:21])[CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 19385051HCID 19385051, compound2×

Product 1

HCID 19385052HCID 19385052, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Hydroxytridecyl)-5-methyl-2(5H)-furanone (Compound 3, 329 mg, 1.11 mmol), acetic anhydride (453 mg, 4.45 mmol), triethylamine (227 mg, 2.22 mmol) and 4-dimethylaminopyridine (2 mg, 0.02 mmol ) were stirred at room temperature under argon for 3 hours in anhydrous THF (30 mL). The crude reaction mixture was concentrated and the residue was taken up in diethyl ether and washed with a 10% aqueous HCl solution, a saturated solution of sodium bicarbonate, H20 and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 20% ethyl acetate/hexane to give the title compound.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. washwashed with a 10% aqueous HCl solution
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil which
  7. customwas purified by flash chromatography on silica using 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1a3fad0fa05347f293a0b4067b084cc7
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

Loading…