5H-Dibenzo[a,d]cyclohepten-5-one → HCID 12690612, compound

HRID 1730968Notes

Reaction equation

HRID 1730968 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH:8]1[C:18]2[CH:17]=[CH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:13](=[O:23])[C:12]=2[CH:11]=[CH:10][CH:9]=1>O1CCCC1.CS(C)=O>[O:23]1[CH2:4][C:13]21[C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[CH:16]=[CH:17][C:18]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]2=1

Participants

6

Reactant 3

HCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 12690612HCID 12690612, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A mixture of 4.6 g. of sodium hydride (57%) and 100 ml. of dimethylsulfoxide is heated under nitrogen at 75° C. for 50 minutes and the resulting mixture treated by addition of 40 ml. tetrahydrofuran and then cooled to 0° C. Over a period of 3 minutes there is then added 10.2 g. of trimethylsulfonium iodide in 100 ml. of dimethylsulfoxide, the resulting mixture stirred for one minute and there is then added over a period of 10 minutes a solution of 16.4 g. of dibenzo[a,d]cyclo-hepten-5-one in 40 ml. of tetrahydrofuran. The resulting mixture is kept overnight at temperature of 5° C. and then stirred for 3 hours at room temperature (20° C.). The mixture is then poured onto 3 times its volume of ice water, extracted twice each with 600 ml. of pentane, the organic phases combined, washed four times with water, dried over anhydrous sodium sulfate and evaporated in vacuo to crystallize spiro[dibenzo[ a,d] cycloheptene-5,2'-oxirane], m.p. 90°-91° C.

Workup

  1. additionA mixture of 4.6 g
  2. additionthe resulting mixture treated by addition of 40 ml
  3. additionOver a period of 3 minutes there is then added 10.2 g
  4. additionthere is then added over a period of 10 minutes a solution of 16.4 g
  5. extractionextracted twice each with 600 ml
  6. washwashed four times with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated in vacuo
  9. customto crystallize spiro[dibenzo[ a,d] cycloheptene-5,2'-oxirane], m.p. 90°-91° C.

Sources & evidence

ORD record
ord-34ae04364bd64bcd83c60b43ba4aa656
Source dataset
uspto-grants-1976_11
Patent number
US03994918

Reaction notes

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