Water → HCID 66991419, compound

HRID 556734Notes

Reaction equation

HRID 556734 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=O.C(P(CCCC)(CCCC)[CH2:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1)CCC.CC([O-])(C)C.[K+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[CH:20][CH:21]1[O:25][CH2:24][CH2:23][O:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 777953HCID 777953, compoundHCID 23665647Potassium tert-butoxideHCID 178454894HCID 178454894, compound

Product 1

HCID 66991419HCID 66991419, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
47 °C

Procedure

3.12 g (12.5 mmol) of 1-(2-Bromo-phenyl)-1H-pyrrole-2-carbaldehyde and 1.2 eqv. of tributyl-[1,3]dioxolan-2-ylmethyl-λ5-phosphane and 1.5 eqv. KOtBu in 20 ml DMSO was stirred for 2 hours. The reaction mixture was heated to 47° C. and stirred over night. The reaction mixture was cooled down to room temperature and poured into 200 ml of water and extracted with diethyl ether, dried over Na2SO4 and the solvent was evaporated. An oily residue was obtained which crystallised over night. The precipitate was washed with diethyl ether, filtered and dried. A mixture of E and Z isomers was obtained. Purification by column chromatography yielded 2 g (50%) of the E isomer 3b.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialdried over Na2SO4
  4. customthe solvent was evaporated
  5. customAn oily residue was obtained which
  6. customcrystallised over night
  7. washThe precipitate was washed with diethyl ether
  8. filtrationfiltered
  9. customdried
  10. additionA mixture of E
  11. customZ isomers was obtained
  12. customPurification by column chromatography

Sources & evidence

ORD record
ord-95686f39f9a846c18c0f52d57a4d9e07
Source dataset
uspto-grants-2011_11
Patent number
US08058306B2

Reaction notes

Loading…