HCID 22826200, compound → HCID 22826201, compound

HRID 325543Notes

Reaction equation

HRID 325543 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C@@H:11]1[O:16][CH:15]([O:17]CC)[CH2:14][C@H:13]([OH:20])[CH2:12]1>C(O)(=O)C.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C@@H:11]1[O:16][CH:15]([OH:17])[CH2:14][C@H:13]([OH:20])[CH2:12]1

Participants

4

Reactant 1

HCID 22826200HCID 22826200, compound

Product 1

HCID 22826201HCID 22826201, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

6(S)-[2-(2,4-dichlorophenyl)-ethyl]-2-ethoxy-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran (0.305 g, 1 mmole) is dissolved in 80% aqueous acetic acid (5 ml) and heated at 70° to 80° for 2 hours. When tlc shows that, the reaction is complete, (if necessary the reaction may be heated at 90° bath temp. for 2 hours). The reaction solution is dissolved in ether and extracted with water, then dilute sodium hydroxide, until washings are basic, and then with water. The ether layer is dried (MgSO4), filtered, and the solvent is evaporated in vacuo to leave 6(S)-[2-(2,4-dichlorophenyl)ethyl]-2-hydroxy-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran.

Workup

  1. temperatureheated at 70° to 80° for 2 hours
  2. custom(if necessary the reaction
  3. temperaturemay be heated at 90° bath temp
  4. extractionextracted with water
  5. dry with materialThe ether layer is dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-ddfa36f15c774873bb2e367fcfcc4ff2
Source dataset
uspto-grants-1984_04
Patent number
US04440927

Reaction notes

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