Methyl 4-chloroacetoacetate → HCID 86745950, compound

HRID 893571Notes

Reaction equation

HRID 893571 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5]([CH2:7][Cl:8])=[O:6].C([C:12]1[CH2:13][S:14][CH2:15][CH2:16][CH:17]=1)=O.S1CCCCC1C([O-])=O>N1CCCCC1.C(O)(=O)C.C(Cl)Cl>[S:14]1[CH2:15][CH2:16][CH2:17][CH2:12][C:13]1=[C:4]([C:5](=[O:6])[CH2:7][Cl:8])[C:3]([O:2][CH3:1])=[O:9]

Participants

7

Reactant 3

HCID 36240Methyl 4-chloroacetoacetateHCID 123752185,6-Dihydro-2H-thiopyran-3-carboxaldehydeHCID 86745951HCID 86745951, compound

Product 1

HCID 86745950HCID 86745950, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl-4-chloroacetoacetate (0.45g) in dry methlene dichlorode (5 ml) containing 4A molecular sieve (3g) was treated with tetrahydrothiapyran-2-carboxylate (0.4g) and then piperidine (2 drops) and acetic acid (2 drops). The mixture was stirred at room temperature for 45 min. The solution was diluted with methylene dichloride and the organic solution washed with water and brine. After drying over anhydrous magnesium sulphate the solvent was evaporated. Chromatography of the residue on silica gel using ethyl acetate-hexane (1:5) as eluant gave the title product as a 2:1 (Z/E) mixture of isomers (0.43g). νmax (CHCl3) 1710 and 1625 cm-1.

Workup

  1. washthe organic solution washed with water and brine
  2. dry with materialAfter drying over anhydrous magnesium sulphate the solvent
  3. customwas evaporated

Sources & evidence

ORD record
ord-4ceb96e745b34aeaafd3217130de4ad1
Source dataset
uspto-grants-1992_06
Patent number
US05126335

Reaction notes

Loading…