Propargyl alcohol → HCID 67148834, compound

HRID 2428088Notes

Reaction equation

HRID 2428088 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[CH:4]=[N:5][OH:6].[CH2:13]1C(=O)N(Cl)[C:15](=[O:16])[CH2:14]1.C(O)C#C.CCN(CC)CC>CN(C=O)C.O.N1C=CC=CC=1>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[C:4]1[CH:13]=[C:14]([CH2:15][OH:16])[O:6][N:5]=1

Participants

8

Reactant 4

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 86246798HCID 86246798, compound

Product 1

HCID 67148834HCID 67148834, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent4×

Procedure

A sol. of 2-chloro-3,6-difluoro-benzaldehyde oxime (21.3 g, 111 mmol) in DMF (66.7 mL) was added dropwise to a sol. of NCS (14.9 g, 111 mmol) and pyridine (1.78 mL) in DMF (222 mL). The mixture was stirred for 1 h at rt, and a sol. of propargyl alcohol (4.99 g, 89.1 mmol) in DMF (71 mL) was dropwise added. The reaction mixture was heated to 85° C., and a sol. of Et3N (15.5 mL, 111 mmol) in DMF (89.3 mL) was slowly added. The reaction mixture was stirred at 85° C. for 60 min, and was allowed to cool to rt. The mixture was diluted with water (533 mL), and was extracted with EtOAc (2×). The combined org. extracts were washed with water and brine, were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 40:60) yielded the title compound (17.0 g, 78%). LC-MS: tR=0.84 min; ES+: 287.12.

Workup

  1. temperatureThe reaction mixture was heated to 85° C.
  2. stirringThe reaction mixture was stirred at 85° C. for 60 min
  3. temperatureto cool to rt
  4. extractionwas extracted with EtOAc (2×)
  5. washextracts were washed with water and brine
  6. dry with materialwere dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification of the residue by FC (EtOAc/heptane 40:60)

Sources & evidence

ORD record
ord-5f5ff7479faf48f389d139af4446c585
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…