3-Chloro-1-propanol → HCID 22715085, compound

HRID 352134Notes

Reaction equation

HRID 352134 reaction equation
C([Mg]Cl)(C)C.Cl[CH2:7][CH2:8][CH2:9][OH:10].[Mg].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=[O:19]>O1CCCC1.BrCCBr>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([OH:19])[CH2:7][CH2:8][CH2:9][OH:10]

Participants

7

Reactant 4

HCID 123133-Chloro-1-propanolHCID 142732-PyridinecarboxaldehydeHCID 5462224MagnesiumHCID 178418918HCID 178418918, compound

Product 1

HCID 22715085HCID 22715085, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

i-Propyl magnesium chloride (11.6 ml, 2M in tetrahydrofuran) was added dropwise to a solution of 3-chloropropanol (2.1 g) in tetrahydrofuran (20 ml) at 0° C. Magnesium turnings (0.8 g) and 1,2-dibromoethane (1 drop) were added and the mixture was refluxed for 5hand then added at 0° C. to a solution of pyridine-2-carboxaldehyde (1.3 g) in tetrahydrofuran (10 ml). The mixture was quenched with aqueous ammonium chloride and basified to pH 9 with aqueous potassium carbonate. Extraction with ethyl acetate and then extraction of the residual inorganics with methanol, followed by evaporation and purification by chromatography on silica eluting with dichloromethane—2M ammonia gave the sub-title compound as a brown oil (1.1 g).

Workup

  1. temperaturethe mixture was refluxed for 5hand
  2. customThe mixture was quenched with aqueous ammonium chloride and basified to pH 9 with aqueous potassium carbonate
  3. extractionExtraction with ethyl acetate
  4. extractionextraction of the residual inorganics with methanol
  5. customfollowed by evaporation and purification by chromatography on silica eluting with dichloromethane—2M ammonia

Sources & evidence

ORD record
ord-08d74f080e6741a0aa6fe9209edffe45
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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