Triethylamine → HCID 15578419, compound

HRID 544174Notes

Reaction equation

HRID 544174 reaction equation
FC(F)(F)S([Cl:6])(=O)=O.[C:9]1([C:15](=[O:27])[CH2:16][C:17](=[O:26])[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl.Cl>[Cl:6][C:18]1[C:17](=[O:26])[CH:16]=[C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[O:27][C:19]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 15578433HCID 15578433, compound

Product 1

HCID 15578419HCID 15578419, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoromethane sulphonyl chloride (3.95 ml) was added over 10 minutes to a stirred solution of ethyl 6-phenyl-2,4,6-trioxohexanoate (8.1 g) and triethylamine (6.5 ml) in dichloromethane (100 ml) at 0° to 5° C. The solution was stirred for 2 hours at 0° to 5° C., then made acidic by passing in hydrogen chloride gas. The mixture was stirred for 3 hours at room temperature, washed with water and evaporated to a brown oil which crystallised from ethanol-water. The product was recrystallised from ethanol-water and from ethyl acetate-petroleum ether 60°-80° C. to give ethyl 3-chloro-4-oxo-6-phenyl-4H-pyran-2-carboxylate (mp 121° C.).

Workup

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. washwashed with water
  3. customevaporated to a brown oil which
  4. customcrystallised from ethanol-water
  5. customThe product was recrystallised from ethanol-water and from ethyl acetate-petroleum ether 60°-80° C.

Sources & evidence

ORD record
ord-5e6622276832410fa853aa406fc16dd6
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

Loading…