Hydrochloric Acid → 3-Azido-3-(6-(trifluoromethyl)pyridin-3-yl)propanal

HRID 241859Notes

Reaction equation

HRID 241859 reaction equation
[N:1]([CH:4]([C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=1)[CH2:5][CH:6]1OCC[O:7]1)=[N+:2]=[N-:3].Cl.C(OCC)C>O1CCCC1>[N:1]([CH:4]([C:11]1[CH:16]=[N:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=1)[CH2:5][CH:6]=[O:7])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 581035825-(1-Azido-2-(1,3-dioxolan-2-yl)ethyl)-2-(trifluoromethyl)pyridine

Product 1

HCID 581035833-Azido-3-(6-(trifluoromethyl)pyridin-3-yl)propanal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(1-azido-2-(1,3-dioxolan-2-yl)ethyl)-2-(trifluoromethyl)pyridine (7.44 g, 25.8 mmol) in tetrahydrofuran (60 mL) was treated with 20% aq. HCl (60 mL) at 0° C. The mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, ethyl ether was added and the organic layer was separated, dried over MgSO4, and concentrated to give a crude oil without further purification.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a crude oil
  6. customwithout further purification

Sources & evidence

ORD record
ord-2aceff42713040ccaea55aa1288cabb1
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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