Dimethyl Sulfoxide → HCID 19434455, compound

HRID 1735858Notes

Reaction equation

HRID 1735858 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([C:14]1([CH2:29][CH2:30][CH2:31][OH:32])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17][C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]1=2)[CH2:12][CH3:13].C(N(CC)CC)C>ClCCl>[CH2:11]([C:14]1([CH2:29][CH2:30][CH:31]=[O:32])[C:15]2[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=2[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]1=2)[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19079070HCID 19079070, compound

Product 1

HCID 19434455HCID 19434455, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

Dissolved oxalyl chloride (1.6 mL, 2.38 g, 0.0187 mol) in 40 mL of dry dichloromethane, and cooled to -78° C. under a nitrogen atmosphere. Added dimethylsulfoxide (2.7 mL, 2.93 g, 0.0374 mol) dissolved in 10 mL of dry dichloromethane dropwise via addition funnel. Stirred for 15 mins at -78° C., and then added 3-[10,11-dihydro-5-propyl-5H-dibenzo[a,d]cyclohepten-5-yl]-propanol (4.41 g, 0.0150 mol) dissolved in 25 mL of dry dichloromethane dropwise via addition funnel. Stirred for 20 mins at -78° C., and then added triethylamine (6.3 mL, 4.55 g, 0.0449 mol). Warmed slowly to room temperature. Added water, and extracted with dichloromethane. Washed combined organic extracts with 0.5N HCl and saturated NaCl, dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 3% ethyl acetate-hexane, 6% ethyl acetate-hexane, and then 10% ethyl acetate-hexane. Combined appropriate fractions, and evaporated to give 3.85 g (88% yield) of 3-[10,11-dihydro-5-propyl-5H-dibenzo[a,d]cyclohepten-5-yl]-propanal as a colorless oil.

Workup

  1. stirringStirred for 20 mins at -78° C.
  2. temperatureWarmed slowly to room temperature
  3. extractionAdded water, and extracted with dichloromethane
  4. washWashed
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurified crude product by flash chromatography on silica gel eluting with 3% ethyl acetate-hexane, 6% ethyl acetate-hexane
  9. customevaporated

Sources & evidence

ORD record
ord-43e9178590444d73837d627cf50e989c
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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