Potassium Carbonate → 3-(4-Benzyloxy-3-methoxyphenyl)-2-ethoxyacrylic acid ethyl ester

HRID 987292

反応式

HRID 987292 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[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[CH2:20]([O:22][CH:23]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH2:27]([O:26][C:24](=[O:25])[C:23]([O:22][CH2:20][CH3:21])=[CH:13][C:12]1[CH:15]=[CH:16][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([O:17][CH3:18])[CH:11]=1)[CH3:28]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)

生成物 1

HCID 537579583-(4-Benzyloxy-3-methoxyphenyl)-2-ethoxyacrylic acid ethyl ester収率 50.7%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
-10 °C

実験手順

4-Benzyloxy-3-methoxybenzaldehyde (7 g; 28.8 mmole) and (1,2-diethoxy-2-oxoethyl) (triphenyl)phosphonium chloride (13.6 g; 31 mmole) was dissolved in isopropanol and the reaction mixture was cooled to −10° C. Potassium carbonate (6 g; 43 mmole) was added. The resulting mixture was stirred over night and the temperature was allowed to reach room temperature. The reaction mixture was filtered and the filtrate was evaporated. Diethyl ether was added to the residue and the resulting mixture was stirred for a while and then insoluble material was filtered off. The filtrate was washed with potassium hydrogensulfate solution and water, dried with magnesium sulfate and evaporated. Isopropylether was added to the residue. Triphenylphosphine oxide precipitated and was filtered off and the filtrate was evaporated. Chromatography of the residue on silica gel using toluene with ethyl acetate (0, 1%, 3%) as eluant gave 5.2 g of 3-(4-benzyloxy-3-methoxyphenyl)-2-ethoxyacrylic acid ethyl ester. Since the product was not pure enough it was stirred with petroleum ether, insoluble material was filtered off and the filtrate was evaporated to give 4 g (38% yield) of pure 3-(4-benzyloxy-3-methoxyphenyl)-2-ethoxyacrylic acid ethyl ester.

後処理

  1. customto reach room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. additionDiethyl ether was added to the residue
  5. stirringthe resulting mixture was stirred for a while
  6. filtrationinsoluble material was filtered off
  7. washThe filtrate was washed with potassium hydrogensulfate solution and water
  8. dry with materialdried with magnesium sulfate
  9. customevaporated
  10. additionIsopropylether was added to the residue
  11. customTriphenylphosphine oxide precipitated
  12. filtrationwas filtered off
  13. customthe filtrate was evaporated

出典と根拠

ORDレコード
ord-67a09b863faa435aa5a303d5089e9680
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

関連ノート

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