Borane;tetrahydrofuran → 5-Methoxy-2-nitro 9H-thioxanthene

HRID 1825781Notes

Reaction equation

HRID 1825781 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[S:5][C:6]1[CH:7]=[CH:8][C:9]([N+:18]([O-:20])=[O:19])=[CH:10][C:11]=1[C:12]2=O.B.C1COCC1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[S:5][C:6]1[CH:7]=[CH:8][C:9]([N+:18]([O-:20])=[O:19])=[CH:10][C:11]=1[CH2:12]2

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 221394365-Methoxy-2-nitro-thioxanthene-9-one

Product 1

HCID 221394015-Methoxy-2-nitro 9H-thioxantheneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) suspension of 5-methoxy-2-nitro-thioxanthene-9-one (24.46 g, 85.13 mmol) in anhydrous tetrahydrofuran (40 ml) under nitrogen atmosphere, was added drop wise borane-THF complex (170 ml, 1.0M in THF). The mixture was allowed to warm to room temperature with stirring overnight. The reaction mixture was cooled (0° C.) and the excess borane was quenched with acetone. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (1:1, dichloromethane/hexane) to give the title compound (11.59 g, 50%) as a bright yellow amorphous solid. 1HNMR (300 MHz, DMSO-d6): δH=3.86 (3H, s), 4.03 (2H, s), 7.00 (2H, dd), 7.28 (1H, t), 7.73 (1H, d), 8.05 (1H, dd), 8.28 (1H, d).

Workup

  1. temperatureTo a cooled
  2. temperatureThe reaction mixture was cooled (0° C.)
  3. customthe excess borane was quenched with acetone
  4. customThe solvent was evaporated in vacuo
  5. customThe residue was purified by flash chromatography (1:1, dichloromethane/hexane)

Sources & evidence

ORD record
ord-eb3ad4dcd984467596d078dd608c49a7
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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