2-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran → HCID 54156467, compound

HRID 905068Notes

Reaction equation

HRID 905068 reaction equation
[Br:1][CH2:2][CH:3]([OH:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11].[Cl:13][C:14]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:15]=1[O:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH:21]=[CH:20][O:19]1>O=P(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:13][C:14]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:15]=1[O:16][CH2:17][C@@H:18]1[O:19][C@@H:20]([O:12][CH:3]([C:4]2[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=2[Cl:11])[CH2:2][Br:1])[CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 130712842-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyranHCID 133860712-Bromo-1-(2,4-dichlorophenyl)ethanol

Product 1

HCID 54156467HCID 54156467, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 24813Phosphorus oxychlorideCatalyst

Procedure

To 10 ml of an ethereal solution of 425 mg of α-bromomethyl-2,4-dichlorobenzyl alcohol and 340 mg of 2-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran was added a catalytic amount (2 drops) of phosphorus oxytrichloride, and the mixture was stirred at room temperature for 4 days. 3 drops of triethylamine were then added and the solvent was evaporated off under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 40:2:1 by volume mixture of hexane, benzene and ethyl acetate, to give 681 mg of the isomer of lesser polarity of trans-6-(2,4-dichlorophenoxymethyl)-2-[2-bromo-1-(2,4-dichlorophenyl)ethoxy]tetrahydropyran as colorless crystals melting at 104°-105° C.

Workup

  1. customthe solvent was evaporated off under reduced pressure
  2. customThe residue was purified by column chromatography through silica gel
  3. washeluted with a 40:2:1 by volume mixture of hexane, benzene and ethyl acetate

Sources & evidence

ORD record
ord-6af0ef801ada4a85967df643069c150f
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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