Cesium carbonate → HCID 54509014, compound

HRID 1762593Notes

Reaction equation

HRID 1762593 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:9]=[C:8]([CH:10]=O)[C:7]=2[CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][CH2:20][O:21][C:22]([CH2:24]P(OCC)(OCC)=O)=[O:23]>O1CCOCC1>[CH2:20]([O:21][C:22](=[O:23])[CH:24]=[CH:10][C:8]1[C:7]2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH:9]=1)[CH3:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13345Triethyl phosphonoacetateHCID 23044216HCID 23044216, compound

Product 1

HCID 54509014HCID 54509014, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.5 g (34 mmol) of 5-methoxybenzocyclobutene-1-carboxaldehyde and 13.8 g (42 mmol) of caesium carbonate are introduced under argon into 55 ml of dioxan. While stirring, 8.7 g (39 mmol) of phosphonoacetic acid triethyl ester are added and the whole is then heated at 80° for 2 hours. The reaction mixture is then concentrated, taken up in dichloromethane and washed with water. The organic phase is dried over sodium sulphate and concentrated by evaporation. The crude product so obtained is purified by chromatography on silica gel. 3-(5-methoxybenzocyclobuten-1-yl)acrylic acid ethyl ester is obtained; Rf=0.5, hexane/diethyl ether (4:1).

Workup

  1. temperaturethe whole is then heated at 80° for 2 hours
  2. concentrationThe reaction mixture is then concentrated
  3. washwashed with water
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customThe crude product so obtained
  7. customis purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9afb0f783c9f4ba6a1b996fd9088acc6
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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