Carbon Dioxide → HCID 54347581, compound

HRID 1900245Notes

Reaction equation

HRID 1900245 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.C(=O)=O.[CH:14]1[C:24]2[CH:23]([CH:25]([CH2:28][CH:29]=[CH2:30])[CH2:26][OH:27])[C:22]3[CH:31]=[CH:32][CH:33]=[CH:34][C:21]=3[CH2:20][O:19][C:18]=2[CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl.O>[CH:14]1[C:24]2[CH:23]([CH:25]([CH2:28][CH:29]=[CH2:30])[CH:26]=[O:27])[C:22]3[CH:31]=[CH:32][CH:33]=[CH:34][C:21]=3[CH2:20][O:19][C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23372177HCID 23372177, compound

Product 1

HCID 54347581HCID 54347581, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

Dissolved oxalyl chloride (3.83 g, 0.0302 mol) in 60 mL of dry dichloromethane, and cooled to -78° C. under a nitrogen atmosphere. Added DMSO (4.3 mL, 4.72 g, 0.0604 mol) dissolved in 15 mL of dry dichloromethane dropwise via addition funnel. CO and CO2 evolution observed. Stirred at -78° C. for 10 mins. Added 2-[6,11-dihydro-dibenzo[b,e]oxepin-11-yl]-pent-4-en-1-ol (6.77 g, 0.0241 mol) dissolved in 50 mL of dry dichloromethane via addition funnel. Stirred at -78° C. for 15 mins. Added triethylamine (10.1 mL, 7.33 g, 0.0724 mol) via addition funnel, and warmed reaction mixture slowly to room temperature. Added 200 mL of water, and separated layers. Extracted aqueous solution with dichloromethane. Washed combined organic extracts with 0.5N HCl, saturated NaCl, dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 10% ethyl acetate-hexane then 15% ethyl acetate-hexane. Combined appropriate fractions and evaporated to give 6.44 g (96% yield) of 2-[6,11-dihydro-dibenzo[b,e]oxepin-11-yl]-pent-4-en-l-al.

Workup

  1. stirringStirred at -78° C. for 15 mins
  2. temperaturewarmed
  3. customreaction mixture slowly to room temperature
  4. customseparated layers
  5. washWashed
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customPurified crude product by flash chromatography on silica gel eluting with 10% ethyl acetate-hexane
  10. customevaporated

Sources & evidence

ORD record
ord-ed60569e25fd45b2b5635e50f3e53ffd
Source dataset
uspto-grants-1996_11
Patent number
US05574173

Reaction notes

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