Potassium Carbonate → HCID 54467866, compound

HRID 1275794Notes

Reaction equation

HRID 1275794 reaction equation
[C:1]1([C:7]2(C=O)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].[O:23]1[CH2:27][CH2:26][O:25][CH:24]1[CH2:28][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:48]([O-])([O-])=O.[K+].[K+].O1CCOC1>C(Cl)Cl.COCCOCCN(CCOCCOC)CCOCCOC.O>[C:1]1([C:7]2([CH:48]=[CH:28][CH:24]3[O:23][CH2:27][CH2:26][O:25]3)[C:19]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]3[C:8]2=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 125861,3-DioxolaneHCID 2724194(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromideHCID 12987276HCID 12987276, compound

Product 1

HCID 54467866HCID 54467866, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-Solvent2×

Procedure

9-Phenyl-9-fluorene carboxaldehyde is dissolved in CH2Cl2 with TDA-1 {tris[2-(2-methoxyethoxy)ethyl]amine} (1 eq). 1,3-dioxolan-2-ylmethyltriphenylphosphonium bromide (1.1 eq) is added followed by a solution of sat. aq K2CO3. The mixture is warmed to reflux and stirred for 15 h. The reaction mixture is diluted with H2O and the resulting mixture is extracted with CH2Cl2. The organic layer is washed consecutively with H2O, 2% aq HCl, and H2O, dried (Na2SO4), and concentrated in vacuo. Purification by liquid chromatography on silica gel affords an E/Z mixture of the dioxolane.

Workup

  1. temperatureThe mixture is warmed
  2. temperatureto reflux
  3. extractionthe resulting mixture is extracted with CH2Cl2
  4. washThe organic layer is washed consecutively with H2O, 2% aq HCl, and H2O
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by liquid chromatography on silica gel
  8. customaffords

Sources & evidence

ORD record
ord-4d69f5de95454759b003c903ed0eaab1
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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