Thioxanthone → 9-cyclopropyl-9H-thioxanthen-9-ol

HRID 863553Notes

Reaction equation

HRID 863553 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+]>C1COCC1.O>[CH:1]1([C:18]2([OH:20])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:11][C:10]3[C:19]2=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10295ThioxanthoneHCID 25517Ammonium ChlorideHCID 178418630HCID 178418630, compound

Product 1

HCID 187993359-cyclopropyl-9H-thioxanthen-9-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of cyclopropylmagnesium bromide in dry THF (prepared from cyclopropylbromide (18.2 g, 0.15 mol), magnesium turnings (2.9 g, 0.12 mol) and dry THF (80 ml)) was placed under an atmosphere of nitrogen. A solution of thioxanthen-9-one (12.7 g, 0.06 mol) in dry THF (70 ml) was added dropwise and when addition was complete the mixture was heated at reflux for 20 minutes. The reaction mixture was cooled on an ice-bath and saturated ammonium chloride (70 ml) was carefully added. The mixture was diluted with water (100 ml) and extracted with diethyl ether (2×100 ml). The combined organic extracts were washed with water, dried (Na2SO4) and the solvent was evaporated in vacuo to give 25.2 g of crude 9-cyclopropyl-9H-thioxanthen-9-ol.

Workup

  1. additionwhen addition
  2. temperaturewas heated
  3. temperatureat reflux for 20 minutes
  4. temperatureThe reaction mixture was cooled on an ice-bath
  5. extractionextracted with diethyl ether (2×100 ml)
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3cdbebf316134a32b21ee4da85b57050
Source dataset
uspto-grants-1998_02
Patent number
US05721254

Reaction notes

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