3-Chloro-1-(4-fluorophenyl)propan-1-ol → Trans-6-(4-fluorophenoxymethyl)-2-[3-chloro-1-(4-fluorophenyl)propoxy]tetrahydropyran

HRID 905085Notes

Reaction equation

HRID 905085 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[OH:5].[F:13][C:14]1[CH:27]=[CH:26][C:17]([O:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH:23]=[CH:22][O:21]2)=[CH:16][CH:15]=1>O=P(Cl)(Cl)Cl.C(OCC)C.C(N(CC)CC)C>[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][C@@H:20]2[O:21][C@@H:22]([O:5][CH:4]([C:6]3[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=3)[CH2:3][CH2:2][Cl:1])[CH2:23][CH2:24][CH2:25]2)=[CH:26][CH:27]=1

Participants

6

Reactant 2

HCID 136395213-Chloro-1-(4-fluorophenyl)propan-1-olHCID 204769402-(4-fluorophenoxymethyl)-3,4-dihydro-2H-pyran

Product 1

HCID 54428102Trans-6-(4-fluorophenoxymethyl)-2-[3-chloro-1-(4-fluorophenyl)propoxy]tetrahydropyranYield 55.2%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 24813Phosphorus oxychlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

One drop of phosphorus oxytrichloride was added to a solution of 222 mg of 3-chloro-1-(4-fluorophenyl)propanol and 233 mg of 2-(4-fluorophenoxymethyl)-3,4-dihydro-2H-pyran in 5 ml of diethyl ether, and the mixture was stirred at room temperature for 2 days. At the end of this time, 2 drops of triethylamine were added, the solvent was evaporated off and the residue was purified by column chromatography through silica gel, to give 245 mg of the title compound.

Workup

  1. customthe solvent was evaporated off
  2. customthe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-6fcf7a0cb4ed41c9aec4b7e9bdb04107
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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