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

HRID 488242

反応式

HRID 488242 の反応式
[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]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 150371484-Phenyl-3-furaldehydeHCID 178443215HCID 178443215、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Dodecylmagnesium bromide (a 1.0 M 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.

後処理

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

出典と根拠

ORDレコード
ord-5809f04bcb0a429c8934fe1bd1b551a3
出典データセット
uspto-grants-1994_03
特許番号
US05298633

関連ノート

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