p-Toluenesulfonic acid → 6-(3-Hydroxyoxetan-3-yl)picolinaldehyde

HRID 931088Notes

Reaction equation

HRID 931088 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[N:11]=[C:10]([C:12]2([OH:16])[CH2:15][O:14][CH2:13]2)[CH:9]=[CH:8][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[OH:16][C:12]1([C:10]2[N:11]=[C:6]([CH:2]=[O:1])[CH:7]=[CH:8][CH:9]=2)[CH2:15][O:14][CH2:13]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 89853573HCID 89853573, compound

Product 1

HCID 898538636-(3-Hydroxyoxetan-3-yl)picolinaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-(6-(1,3-dioxolan-2-yl)pyridin-2-yl)oxetan-3-ol (67 mf, 0.30 mmol) and p-toluenesulphonic acid (14.8 mg, 0.26 mmol) in acetone (3.00 mL) was heated to 50° C. and stirred for 18 h. The reaction mixture was cooled to room temperature. The solvent was removed under reduced pressure to afford the title compound. The material was used without further purification. MS (ES+) (M+H) 180.0; LCMS retention time: 1.57 minutes (Method L).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6f07fe5e01cd4d50a70cd445a0a38a1f
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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