2-Bromo-1-(4-chlorophenyl)ethan-1-ol → trans-6-(2,4-Dichlorophenoxymethyl)-2-[2-bromo-1-(4-chlorophenyl)ethoxy]tetrahydropyran

HRID 905070Notes

Reaction equation

HRID 905070 reaction equation
[Br:1][CH2:2][CH:3]([OH:11])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:14]=1[O:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH:20]=[CH:19][O:18]1>C(OCC)C.O=P(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:12][C:13]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:14]=1[O:15][CH2:16][C@@H:17]1[O:18][C@@H:19]([O:11][CH:3]([C:4]2[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=2)[CH2:2][Br:1])[CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 2

HCID 2368002-Bromo-1-(4-chlorophenyl)ethan-1-olHCID 130712842-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran

Product 1

HCID 53718043trans-6-(2,4-Dichlorophenoxymethyl)-2-[2-bromo-1-(4-chlorophenyl)ethoxy]tetrahydropyranYield 30.3%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 24813Phosphorus oxychlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 259 mg of α-bromomethyl-4-chlorobenzyl alcohol and 311 mg of 2-(2,4-dichlorophenoxymethyl)-3,4-dihydro-2H-pyran in 6 ml of diethyl ether was added one drop of phosphorus oxytrichloride, and the mixture was stirred at room temperature for 1 day. After 3 drops of triethylamine had been added, the solvent was evaporated off under reduced pressure and the residue was purified by column chromatography through silica gel eluted with a 5:50:11 by volume mixture of benzene, hexane and ethyl acetate, to give 147 mg of the isomer of lesser polarity of trans-6-(2,4-dichlorophenoxymethyl)-2-[2-bromo-1-(4-chlorophenyl)ethoxy]tetrahydropyran melting at 86°-87° C., 165 mg of the isomer of greater polarity melting at 97°-98° C., and 80 mg of a mixture thereof.

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 5:50:11 by volume mixture of benzene, hexane and ethyl acetate

Sources & evidence

ORD record
ord-cdf87a7c11d84c979c5af835a820cb6a
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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