Borane;tetrahydrofuran → HCID 22139408, compound

HRID 1825786Notes

Reaction equation

HRID 1825786 reaction equation
[Br:1][C:2]1[C:15]2[C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1.B.C1COCC1>O1CCCC1>[Br:1][C:2]1[C:15]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 22139414HCID 22139414, compound

Product 1

HCID 22139408HCID 22139408, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled 0° C.) suspension of 1-bromo-4-hydroxy-thioxanthen-9-one (24.23 g, 78.88 mmol) in anhydrous tetrahydrofuran (40 ml) under nitrogen atmosphere, was added dropwise borane-THF complex (237 ml, 1M in THF). The cloudy mixture was allowed to warm to room temperature and was left stirring overnight. The suspension dissolved gradually as the reaction progressed giving a yellow solution. The reaction mixture was cooled (0° C.) and the excess borane was quenched with acetone. The yellow solution was evaporated in vacuo. The resulting oil was purified by flash chromatography (4:1, hexane/ethyl acetate) to give the title compound (11.50 g, 50%). m/z (LC-MS, ESP), RT=4.84 min, (M−−1)=291–293.

Workup

  1. waitwas left
  2. dissolutionThe suspension dissolved gradually as the reaction
  3. customprogressed giving a yellow solution
  4. temperatureThe reaction mixture was cooled (0° C.)
  5. customthe excess borane was quenched with acetone
  6. customThe yellow solution was evaporated in vacuo
  7. customThe resulting oil was purified by flash chromatography (4:1, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0dea2572423a4f6a906b9d66b6d9bad0
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

Loading…