Dimethyl Sulfoxide → HCID 283964, compound

HRID 1651057Notes

Reaction equation

HRID 1651057 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C:12]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=[CH:16][C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=2[CH:13]=1.C(N(CC)CC)C>ClCCl>[O:11]=[C:12]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH:17]=[CH:16][C:15]2[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=2[CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67794808HCID 67794808, compound

Product 1

HCID 283964HCID 283964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (5 ml) in dry dichloromethane (75 ml) at -78° C. under nitrogen was added, dropwise. dimethyl sulphoxide (8.75 ml), and the solution stirred at -78° C. for 15 minutes. A solution of 5-hydroxy-dibenzo[a,e]cyclooctene (11.1 g) in dichloromethane (75 ml) was added over 5 minutes at -78° C. and the solution stirred for 15 minutes, then triethylamine (30 ml) was added and the mixture allowed to warm to room temperature. The mixture was washed with water (100 ml), 1N hydrochloric acid (50 ml) water (100 ml), brine (50 ml) then dried and evaporated to give the crude ketone which was recrystallised from ethyl alcohol/hexane (10.0 g), mp 112°-6 ° C.

Workup

  1. washThe mixture was washed with water (100 ml), 1N hydrochloric acid (50 ml) water (100 ml), brine (50 ml)
  2. customthen dried
  3. customevaporated

Sources & evidence

ORD record
ord-faaa5d1edf2042d2b43a927746370721
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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