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

HRID 353298Notes

Reaction equation

HRID 353298 reaction equation
[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

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)HCID 22708428[4-Benzyl-3-(benzyloxy)phenyl]methanol

Product 1

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

Procedure

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.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationThe precipitate was filtered off
  3. customthe solvent evaporated in vacuo
  4. customPurification of the crude product with preparative HPLC (Kromasil C8, 10 μm, 50×500 mm)

Sources & evidence

ORD record
ord-394eb0a22a3944fea765b36aa7ad295a
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Reaction notes

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