Borane → Thioxanthene

HRID 1935321Notes

Reaction equation

HRID 1935321 reaction equation
[CH:1]1[C:14]2[C:13](=O)[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.B>C1COCC1>[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 10295Thioxanthone

Product 1

HCID 67495Thioxanthene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Thioxanthen-9-one, 28 (14.0 g, 66.0 mmol) was dissolved in THF (186 mL). While under argon, the solution was treated dropwise with 1.0M borane in THF (50 mL, 50.0 mmol) and refluxed (3 hrs). The reaction mixture was cooled, poured into ice (300 g) and extracted with ethyl acetate (3×350 mL). The extracts were combined, washed with brine (1×), dried over Na2SO4, filtered and concentrated to dryness in vacuo. Treatment of the resulting oil with methanol gave the title compound as a white solid.

Workup

  1. temperaturerefluxed (3 hrs)
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate (3×350 mL)
  4. washwashed with brine (1×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-37a34257471c42a19eea1ba66383c87e
Source dataset
uspto-grants-2002_05
Patent number
US06387893B1

Reaction notes

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