Acetic Acid → HCID 68616271、化合物

HRID 353308

反応式

HRID 353308 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:19].CC(C)([O-])C.[K+].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[C:21](\[O:20][CH2:18][CH3:19])/[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 69955Ethyl ethoxyacetateHCID 202986464-(Benzyloxy)-3-methylbenzaldehydeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 68616271HCID 68616271、化合物収率 25%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

4-(Benzyloxy)-3-methylbenzaldehyde (2.36 g; 10.2 mmole) and ethyl ethoxyacetate (1.62 g; 12.3 mmole) were dissolved in dry THF (10 ml) and cooled to −20° C. Potassium tert-butoxide (1.38 g; 12.3 mmole) dissolved in dry tetrahydrofuran (1 ml) was slowly added and the reaction was stirred over night at −20° C. The reaction was quenched with acetic acid (0.80 g; 13.3 mmole). The crude product was isolated, redissolved in toluene and refluxed overnight with p-toluenesulfonic acid (0.18 g; 1.0 mmole) in a Dean-Stark apparatus to separate the water. The solution was cooled, washed with sodium hydrogen carbonate, dried with magnesium sulfate and evaporated. Purification of the crude product with preparative HPLC (Kromasil C8, 10 μm, 50×500 mm) using acetronitrile (50-100%) in ammonium acetate buffer (pH 7) as mobile phase gave 0.86 g (25% yield) of ethyl (2Z)-3-[4-(benzyloxy)-3-methylphenyl]-2-ethoxyacrylate.

後処理

  1. additionwas slowly added
  2. customThe crude product was isolated
  3. customto separate the water
  4. temperatureThe solution was cooled
  5. washwashed with sodium hydrogen carbonate
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customPurification of the crude product with preparative HPLC (Kromasil C8, 10 μm, 50×500 mm)

出典と根拠

ORDレコード
ord-df3f7efd7d2142ceac1d36c76767c65b
出典データセット
uspto-grants-2004_06
特許番号
US06750252B2

関連ノート

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