Ethyl Acetate → HCID 62469629, compound

HRID 1819390Notes

Reaction equation

HRID 1819390 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[CH:4][N:3]=1.C1C=CC(P([N:24]=[N+:25]=[N-:26])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1.CCOC(C)=O>C1(C)C=CC=CC=1.Cl.CCOCC>[N:24]([CH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)=[N+:25]=[N-:26]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 2763647(2-Chloropyridin-3-yl)methanol

Product 1

HCID 62469629HCID 62469629, compoundYield 78.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of the above (2-chloro-pyridin-3-yl)-methanol (2.2 g, 15.1 mmol) and DPPA (3.9 mL, 18.2 mmol) in toluene (30 mL) was added DBU (2.9 mL, 18.2 mmol) at room temperature and stirred for 3 h. The reaction was diluted with 3M HCl (30 mL) and Et2O (75 mL). The layers were separated and the aqueous layer was extracted with Et2O (75 mL). The combined organic layers were washed with water (50 mL), brine and dried over MgSO4. The solution was filtered and concentrated in vacuo to yield a yellow oil. Silica gel column chromatography using 95:5 hexanes:EtOAc afforded 2.0 g (77%) of 3-azidomethyl-2-chloro-pyridine as a colorless oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with Et2O (75 mL)
  3. washThe combined organic layers were washed with water (50 mL), brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto yield a yellow oil

Sources & evidence

ORD record
ord-828142fa2ab442b7a17477cebf680bab
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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