Borane;tetrahydrofuran → HCID 86635142, compound

HRID 1908253Notes

Reaction equation

HRID 1908253 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)=[O:6])=[N+:2]=[N-:3].B.C1COCC1>C1COCC1>[N:1]([CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)[OH:6])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 161273432-Azido-1-(4-methylsulfanyl-phenyl)-ethanone

Product 1

HCID 86635142HCID 86635142, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution consisting of 2-azido-1-(4-methylsulfanyl-phenyl)-ethanone (1.69 g, 8.15 mmol) and THF (8.15 mL) was cooled to 0° C. before slowly adding BH3.THF (1.0 M solution, 8.15 ml) over 10 min. The resulting solution was stirred at 0° C. for 2 h. The reaction was quenched by slow addition of MeOH (10 mL) at 0° C., and then concentrating to dryness to yield the title compound (1.74 g, 100%).

Workup

  1. customThe reaction was quenched by slow addition of MeOH (10 mL) at 0° C.
  2. concentrationconcentrating to dryness

Sources & evidence

ORD record
ord-fb1626e1d9964792a55b3792c5628738
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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