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

HRID 657742Notes

Reaction equation

HRID 657742 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 yield 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 yield a crude oil
  6. customwithout further purification

Sources & evidence

ORD record
ord-98e39de7d19e41a8a0d2a4f57870e4f5
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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