Carbon Dioxide → HCID 19079048, compound

HRID 1735863Notes

Reaction equation

HRID 1735863 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C]=O.C(=O)=O.[CH2:16]([O:18][C:19]1([CH2:34][CH2:35][OH:36])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][O:22][C:21]2[CH:30]=[CH:31][CH:32]=[CH:33][C:20]1=2)[CH3:17].C(N(CC)CC)C>ClCCl.O>[CH2:16]([O:18][C:19]1([CH2:34][CH:35]=[O:36])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][O:22][C:21]2[CH:30]=[CH:31][CH:32]=[CH:33][C:20]1=2)[CH3:17]

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19434456HCID 19434456, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 19079048HCID 19079048, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

Dissolved oxalyl chloride (3.62 g, 2.5 mL, 0.0285 mol) in 30 mL of dry dichloromethane, and cooled to -78° C. under a nitrogen atmosphere. Added dimethylsulfoxide (4.45 g, 4.0 mL, 0.0570 mol) in 10 mL of dry dichloromethane dropwise via addition funnel. Carbon monoxide and carbon dioxide evolution observed. Stirred at -78° C. for 15 mins. Added 2-[6,11-dihydro-11-ethoxydibenz[b,e]oxepin-11-yl]-ethanol (6.75 g, 0.0237 mol) dissolved in 30 mL of dry dichloromethane dropwise via addition funnel. Stirred at -78° C. for 15 mins. then added triethylamine (7.21 g, 9.9 mL, 0.0712 mol). Warmed slowly to room temperature. Added 150 mL of water, and separated layers. Extracted aqueous solution with dichloromethane. Washed combined organic extracts with 0.5N HCl and then saturated NaCl, dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 5% ethyl acetatehexane then 10% ethyl acetate-hexane. Combined appropriate fractions, and evaporated to give 3.47 g (52% yield) of 2-[6,11-dihydro-11-ethoxydibenz[b,e]oxepin-11-yl]-ethanal as a colorless oil.

Workup

  1. stirringStirred at -78° C. for 15 mins
  2. temperatureWarmed slowly to room temperature
  3. customseparated layers
  4. washWashed
  5. dry with materialsaturated NaCl, dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurified crude product by flash chromatography on silica gel eluting with 5% ethyl acetatehexane
  9. customevaporated

Sources & evidence

ORD record
ord-347be04b4e19443eba9278d69b62e8b4
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

Loading…