Acetic Anhydride → 3(-1-Acetoxytridecyl)-4-phenylfuran

HRID 273957

Reaction equation

HRID 273957 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:15]1([C:21]2[C:22]([CH:26]=[O:27])=[CH:23][O:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C1COCC1>[C:28]([O:27][CH:26]([C:22]1[C:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:25][O:24][CH:23]=1)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 150371484-Phenyl-3-furaldehydeHCID 178443215HCID 178443215, compound

Product 1

HCID 150371563(-1-Acetoxytridecyl)-4-phenylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dodecylmagnesium bromide (a 1.0M solution in THF; 2.11 ml, 2.11 mmol) was added to a solution of 4-phenyl-3-furaldehyde (303 mg, 1.76 mmol) in THF at 0 degrees under argon and gradually allowed to warm to room temperature with stirring. When all of the aldehyde was consumed acetic anhydride (719 mg, 7.04 mmol) was added and stirring was continued for 2 hours more. The reaction was quenched with saturated ammonium chloride and the organics were extracted into ethyl ether. The combined fractions were washed with saturated sodium bicarbonate, water and brine, dried over magnesium sulfate and concentrated to a yellow oil which was purified by flash chromatography on silica using 3% ethyl ether hexanes to give the title compound.

Workup

  1. additionwas added
  2. stirringstirring
  3. customThe reaction was quenched with saturated ammonium chloride
  4. extractionthe organics were extracted into ethyl ether
  5. washThe combined fractions were washed with saturated sodium bicarbonate, water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to a yellow oil which
  8. customwas purified by flash chromatography on silica using 3% ethyl ether hexanes

Sources & evidence

ORD record
ord-b1812e3a919a44a88201410d57a6b28c
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Linked notes

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