3-Hydroxymethyldibenzo[b,f]thiepin 5-oxide → Dibenzo[b,f]thiepin-3-carboxaldehyde-5-oxide

HRID 485101Notes

Reaction equation

HRID 485101 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8](=[O:17])[C:7]=2[CH:18]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH:5]1[C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8](=[O:17])[C:7]=2[CH:18]=[C:3]([CH:2]=[O:1])[CH:4]=1

Participants

4

Reactant 2

HCID 133326573-Hydroxymethyldibenzo[b,f]thiepin 5-oxideHCID 178418287HCID 178418287, compound

Product 1

HCID 13520246Dibenzo[b,f]thiepin-3-carboxaldehyde-5-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 512 mg (2 mmole) of 3-hydroxymethyldibenzo[b,f]thiepin 5-oxide in 50 ml of methylene chloride and add 648 mg (3 mmole) of pyridinium chlorochromate. Stir at room temperature for 1.5 hours and then filter the mix through a bed of Florisil. Wash the Florisil with dichloromethane; and to the combined filtrate add 4 g of silica gel. Evaporate the suspension to dryness, and place the solid on top of a column of 50 g of silica and elute the title compound with a 1:9 mixture of ethyl acetate and toluene. The compound has a m.p. of 188°-190° C.

Workup

  1. filtrationfilter the
  2. additionmix through a bed of Florisil
  3. washWash the Florisil with dichloromethane
  4. additionand to the combined filtrate add 4 g of silica gel
  5. customEvaporate the suspension to dryness
  6. washelute the title compound
  7. additionwith a 1:9 mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-eb40fd7f811a4fb18be9e79f645cb73e
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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