Phosphorus oxychloride → trans-6-(2,4-Dichlorphenoxymethyl)-2-[1-chloro-4-(2,4-dichlorophenyl)-2-butoxy]tetrahydropyran

HRID 905080Notes

Reaction equation

HRID 905080 reaction equation
O=P(Cl)(Cl)Cl.[Cl:6][C:7]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:8]=1[O:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH:14]=[CH:13][O:12]1.[Cl:22][CH2:23][CH:24]([OH:35])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34]>C(OCC)C.C(N(CC)CC)C>[Cl:6][C:7]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:8]=1[O:9][CH2:10][C@@H:11]1[O:12][C@@H:13]([O:35][CH:24]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])[CH2:23][Cl:22])[CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 130712842-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyranHCID 204768722,4-Dichloro-alpha-(chloromethyl)benzenepropanol

Product 1

HCID 22824900trans-6-(2,4-Dichlorphenoxymethyl)-2-[1-chloro-4-(2,4-dichlorophenyl)-2-butoxy]tetrahydropyran

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 3283Diethyl EtherSolvent

Procedure

2 Drops of phosphorus oxytrichloride were added to a solution of 388 mg of 2-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran and 418 mg of 1-chloro-4-(2,4-dichlorophenyl)-2-butanol in 8 ml of diethyl ether, and the mixture was allowed to react at room temperature for 2 days. At the the end of this time, 3 drops of triethylamine were added and the solvent was evaporated off. The residue was purified by column chromatography through silica gel eluted with a 50:5:1 by volume mixture of hexane, benzene and ethyl acetate, to give 185 mg of the isomer of lesser polarity of trans-6-(2,4-dichlorphenoxymethyl)-2-[1-chloro-4-(2,4-dichlorophenyl)-2-butoxy]tetrahydropyran and 153 mg of the isomer of greater polarity.

Workup

  1. customto react at room temperature for 2 days
  2. customthe solvent was evaporated off
  3. customThe residue was purified by column chromatography through silica gel
  4. washeluted with a 50:5:1 by volume mixture of hexane, benzene and ethyl acetate

Sources & evidence

ORD record
ord-02b30c8cfaa74719b23b1771b78414b5
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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