Pyridine → HCID 13517254, compound

HRID 1981046Notes

Reaction equation

HRID 1981046 reaction equation
[CH2:1]([CH:4]1[C:8]([OH:10])([CH3:9])[CH:7]=[CH:6][C:5]1=[O:11])[CH:2]=[CH2:3].N1C=CC=CC=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].C(Cl)(=O)C>O.ClCCl>[CH2:1]([CH:4]1[C:8]([O:10][C:20](=[O:21])[CH2:19][Cl:18])([CH3:9])[CH:7]=[CH:6][C:5]1=[O:11])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 6577Chloroacetyl chlorideHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 13517254HCID 13517254, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Into the same flask as in Example 1, dl-2-allyl-3-hydroxy-3-methyl-4-cyclopentenone (15.2 g), pyridine (15 g) and dichloromethane (150 g) were charged, and chloroacetyl chloride (22.5 g) was dropwise added thereto at a temperature from 10° to 15° C. in 3 hours. Then, stirring was continued at room temperature for 24 hours. To the reaction mixture kept below 10° C., water (50 ml) was added to decompose excess of acetyl chloride. The resulting mixture was treated as in Example 1. The residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate (10:1) as an eluent to give dl-2-allyl-3-chloroacetyloxy-3-methyl-4-cyclopentenone (20.7 g). Yield, 91%.

Workup

  1. waitwas continued at room temperature for 24 hours
  2. customkept below 10° C.
  3. additionThe resulting mixture was treated as in Example 1
  4. customThe residue was purified by silica gel chromatography
  5. additiona mixture of toluene and ethyl acetate (10:1) as an eluent

Sources & evidence

ORD record
ord-1e8d8491780b4609a8aea8809ea58fce
Source dataset
uspto-grants-1985_04
Patent number
US04511655

Reaction notes

Loading…