Potassium Carbonate → 3-Hydroxybutyl 4-methylbenzenesulfonate

HRID 1601272Notes

Reaction equation

HRID 1601272 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].F[C:13]1C=C[C:16]2C(C3CCNCC3)=N[O:19][C:15]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O:4][CH2:13][CH2:14][CH:15]([OH:19])[CH3:16])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 85570p-ToluenesulfonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 132043233-Hydroxybutyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Racemic 3-hydroxybutyl tosylate was prepared in a manner described by Ferreira et al., Tetrahedron, 46, pp. 6311-6318, (1990). To a solution of the racemic tosylate (9.2 g, 37.7 mmol) in acetonitrile (190 ml) was added 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (8.3 g, 37.7 mmol) followed by milled potassium carbonate (7.8 g, 56.6 mmol) at room temperature under nitrogen. The reaction mixture was warmed to reflux for 4.5 hours and allowed to cool to room temperature. The solids were removed via filtration through a pad of Celite and were washed with EtOAc. The combined filtrates were concentrated to give the crude product. Purification via preparative HPLC (silica gel, 10% MeOH/EtOAc) afforded 6.3 g (57%), m.p.=100-102° C.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for 4.5 hours
  3. customThe solids were removed via filtration through a pad of Celite
  4. washwere washed with EtOAc
  5. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-f365e2b2a6ba45a3801e3ae85a5ff8b4
Source dataset
uspto-grants-1999_11
Patent number
US05977113

Reaction notes

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