1,8-Diazabicyclo(5.4.0)undec-7-ene → E-4-Pentyloxy-1-[4-(1-imidazolylmethyl)phenyl]but-1-en-3-one

HRID 978413Notes

Reaction equation

HRID 978413 reaction equation
[O:1]=[C:2]([CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3]P(OC)(=O)OC.[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[CH2:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.C1CCN2C(=NCCC2)CC1>C(COC)OC>[CH2:12]([O:11][CH2:10][C:2](=[O:1])/[CH:3]=[CH:27]/[C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C:18]2[NH:19][CH:20]=[CH:21][N:17]=2)=[CH:30][CH:29]=1)[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13590432Dimethyl 2-oxo-3-pentyloxypropanephosphonateHCID 867414844-(1-Imidazolylmethyl)benzaldehyde

Product 1

HCID 86741483E-4-Pentyloxy-1-[4-(1-imidazolylmethyl)phenyl]but-1-en-3-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2 g (7.93 mmol) of dimethyl 2-oxo-3-pentyloxypropanephosphonate, 1.7 g (9.13 mmol) of 4-(1-imidazolylmethyl)benzaldehyde and 1.33 g (8.74 mmol) of DBU were stirred in 150 ml of dimethoxyethane at room temperature for 31 h. The mixture was filtered through silica gel and the solvent was removed from the filtrate in vacuo. Chromatography on silica gel (chloroform/methanol/25% aqueous NH3 =20/1/0.2) produced 1.5 g (4.80 mmol, 60%) as a yellowish oil which solidified in the refrigerator, melting point 35°-36° C.

Workup

  1. filtrationThe mixture was filtered through silica gel
  2. customthe solvent was removed from the filtrate in vacuo
  3. customChromatography on silica gel (chloroform/methanol/25% aqueous NH3 =20/1/0.2) produced 1.5 g (4.80 mmol, 60%) as a yellowish oil which

Sources & evidence

ORD record
ord-bcb062ab8c9a428d8fb8f11a8dea4f19
Source dataset
uspto-grants-1987_05
Patent number
US04665080

Reaction notes

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