Pyridine → 6-[2-(2-acetoxy-4,6-dichlorophenyl)ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

HRID 354578Notes

Reaction equation

HRID 354578 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([OH:13])[C:7]=1[CH2:14][CH2:15][CH:16]1[O:21][C:20](=[O:22])[CH2:19][CH:18]([OH:23])[CH2:17]1.N1C=CC=CC=1>CCOCC>[C:1]([O:13][C:8]1[CH:9]=[C:10]([Cl:12])[CH:11]=[C:6]([Cl:5])[C:7]=1[CH2:14][CH2:15][CH:16]1[O:21][C:20](=[O:22])[CH2:19][CH:18]([OH:23])[CH2:17]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 135531966-{2-(2,4-Dichloro-6-hydroxyphenyl)-ethyl}-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

Product 1

HCID 201590396-[2-(2-acetoxy-4,6-dichlorophenyl)ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

Acetyl chloride (0.08 ml, 1.05 mmole) was added dropwise to a stirred solution of 6-[2-(2,4-dichloro-6-hydroxyphenyl)ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (300 mg, 1 mmole) and pyridine (0.09 ml, 1.05 mmole) in ether (10 ml) at 0° C. The ice bath was removed and the reaction mixture was stirred at 20° C. for 1 hour and then diluted with H2O (10 ml). The organic layer was separated and washed with 1 N HCl (10 ml), H2O (2×10 ml) and brine, dried over MgSO4, filtered and evaporated to provide the title compound.

Workup

  1. customThe ice bath was removed
  2. additiondiluted with H2O (10 ml)
  3. customThe organic layer was separated
  4. washwashed with 1 N HCl (10 ml), H2O (2×10 ml) and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d393fa6ff752410096f41d2e68965b80
Source dataset
uspto-grants-1983_03
Patent number
US04375475

Reaction notes

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