Isopropanol → Ethyl (E)-3-[3-benzyl-4-(benzyloxy)phenyl]-2-ethoxy-2-propenoate

反応式

[CH2:1]([C:8]1[CH:13]=[CH:12][C:11](CO)=[CH:10][C:9]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[CH2:25]([O:27][CH:28]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:29](OCC)=O)[CH3:26].[C:53](=[O:56])([O-])[O-:54].[K+].[K+].[CH:59](O)(C)[CH3:60]>>[CH2:1]([C:8]1[CH:13]=[C:12](/[CH:26]=[C:25](/[O:27][CH2:28][CH3:29])\[C:53]([O:54][CH2:59][CH3:60])=[O:56])[CH:11]=[CH:10][C:9]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

反応物 4

HCID 3776Isopropanol

HCID 11430Potassium Carbonate

HCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)

HCID 22708428[4-Benzyl-3-(benzyloxy)phenyl]methanol

生成物 1

HCID 86588957Ethyl (E)-3-[3-benzyl-4-(benzyloxy)phenyl]-2-ethoxy-2-propenoate収率 46%

実験手順

Compound (c) and (1,2-diethoxy-2-oxoethyl)(triphenyl)phosphonium chloride (2.89 g, 6.74 mmole) were dissolved in isopropanol (100 ml) and anhydrous potassium carbonate (1.24 g, 9.00 mmole) was added and the mixture was refluxed overnight. The precipitate was filtered off and the solvent evaporated in vacuo. Purification of the crude product with preparative HPLC (Kromasil C8, 10 μm, 50×500 mm) using acetronitrile (50-70%) in ammonium acetate buffer (pH 7) as mobile phase gave 0.88 g (46% yield) of the desired product.