Acetic Acid → Methyl 2-acetyl-3,5-diallyloxyphenylacetate

HRID 495180

反応式

HRID 495180 の反応式
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3].[C:20](O)(=[O:22])[CH3:21].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[C:20]([C:8]1[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[CH:10][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:6][C:7]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:22])[CH3:21]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 23116191Methyl 3,5-diallyloxyphenylacetate

生成物 1

HCID 68421776Methyl 2-acetyl-3,5-diallyloxyphenylacetate収率 70.4%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
4 °C

実験手順

Methyl 3,5-diallyloxyphenylacetate (40 g, 0.14 mol) obtained in Example 5, Step 1 was dissolved in trifluoroacetic acid (0.15 L). After the solution was cooled to 4° C., acetic acid (9.5 mL, 0.17 mol) and trifluoroacetic anhydride (40 mL, 0.28 mol) were added thereto, followed by stirring at 4° C. for 3.5 hours. The reaction mixture was gradually added to a saturated aqueous solution of sodium hydrogencarbonate for neutralization, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/20-1/6) to obtain methyl 2-acetyl-3,5-diallyloxyphenylacetate (30 g, 65%). 1H-NMR (CDCl3, 300 MHz) δ (ppm): 6.43 (d, J=2.2 Hz, 1H), 6.37 (d, J=2.2 Hz, 1H), 6.07-5.98 (m, 2H), 5.44-5.27 (m, 4H), 4.57-4.52 (m, 4H), 3.69 (s, 2H), 3.68 (s, 3H), 2.53 (s, 3H)

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/20-1/6)

出典と根拠

ORDレコード
ord-d7b2a0324f5548dfb1e51811df6fdf0b
出典データセット
uspto-grants-2009_05
特許番号
US07538224B2

関連ノート

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