1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(4-Benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl ester

HRID 479195Notes

Reaction equation

HRID 479195 reaction equation
[Cl-].[CH2:2]([O:4][CH:5]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:3].C1CCN2C(=NCCC2)CC1.[CH2:41]([O:48][C:49]1[C:54]2[CH:55]=[CH:56][O:57][C:53]=2[C:52]([CH:58]=O)=[CH:51][CH:50]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1COCC1>[CH2:9]([O:8][C:6](=[O:7])/[C:5](/[O:4][CH2:2][CH3:3])=[CH:58]/[C:52]1[C:53]2[O:57][CH:56]=[CH:55][C:54]=2[C:49]([O:48][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:50][CH:51]=1)[CH3:10]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)2×HCID 226476054-Benzyloxy-benzofuran-7-carbaldehyde

Product 1

HCID 686170643-(4-Benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride (2.04 g, 4.8 mmol) and DBU (0.8 g, 5.2 mmol) in THF (40 ml) was stirred for 10 min at ambient temperature under an argon atmosphere [for the preparation of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride see: K. K. Bach, H. R. El-Seedi, H. M. Jensen, H. B. Nielsen, I. Thomson, K. B. G. Torssell, Tetrahedron 1994, 50, 7543-7556]. 4-Benzyloxy-benzofuran-7-carbaldehyde (0.8 g, 3.2 mmol) was added and the mixture was heated under reflux for 12 h. The solvent was concentrated at reduced pressure, the residue taken up with ethyl acetate, washed with saturated aqueous NH4Cl solution and two times with brine. The organic layer was dried over sodium sulfate, the solvent removed under reduced pressure and the residue purified by column chromatography (silica gel, hexane/AcOEt=9/1) to give 0.8 g (2.2 mmol, 69%) of the title compound as colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 h
  3. concentrationThe solvent was concentrated at reduced pressure
  4. washwashed with saturated aqueous NH4Cl solution and two times with brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent removed under reduced pressure
  7. customthe residue purified by column chromatography (silica gel, hexane/AcOEt=9/1)

Sources & evidence

ORD record
ord-c134086984bb4904b030b4881901d2ac
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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