Sodium hydride → HCID 21415005, compound

HRID 328540Notes

Reaction equation

HRID 328540 reaction equation
[C:1]1(CC=O)C2C3CCC(C4C3=CC=CC=4)C=2C=CC=1.[I-].C[S+](C)(C)=O.[H-].[Na+].[H][H].[CH:30]1[C:43]2[C:42]3([CH2:46][CH:47]=[O:48])[CH2:44][CH2:45][CH:35]([C:36]4[C:41]3=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:34]=2[CH:33]=[CH:32][CH:31]=1>CS(C)=O.O>[O:48]1[CH2:1][CH:47]1[CH2:46][C:42]12[CH2:44][CH2:45][CH:35]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=31)[C:34]1[C:43]2=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 53657819HCID 53657819, compoundHCID 54460731HCID 54460731, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21415005HCID 21415005, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To convert the aldehyde into the epoxide, 19.6 g of trimethyloxosulphonium iodide are added to 2.2 g of sodium hydride in 175 ml of dimethyl sulphoxide. When evolution of hydrogen has ceased, a solution of 21 g of the crude 9,10-dihydro-9,10-ethano-9-anthryl-acetaldehyde in 35 ml of dimethyl sulphoxide is added dropwise and the batch is stirred for 20 minutes at room temperature and then for 30 minutes at 55°-60° C. The reaction mixture is then poured into 300 ml of water and after extraction with methylene chloride, the methylene chloride solution is isolated and evaporated to yield as residue the crude 9-(2,3-epoxy-propyl)-9,10-dihydro-9,10-ethano-anthracene in the form of a viscous oil.

Workup

  1. waitfor 30 minutes at 55°-60° C
  2. extractionafter extraction with methylene chloride
  3. customthe methylene chloride solution is isolated
  4. customevaporated

Sources & evidence

ORD record
ord-dea2b55e87e94adb8edcc92664b236a2
Source dataset
uspto-grants-1977_04
Patent number
US04017542

Reaction notes

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