2,4-Dichlorobenzyl alcohol → trans-6-(2,4-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

HRID 905055

Reaction equation

HRID 905055 reaction equation
[S:1]([O:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][O:14]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Cl:19][C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[CH2:22][OH:23]>C(OCC)C.O=P(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:19][C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[CH2:22][O:23][C@@H:15]1[O:14][C@@H:13]([CH2:12][O:11][S:1]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=2)(=[O:3])=[O:2])[CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 2

HCID 156842,4-Dichlorobenzyl alcoholHCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 13073916trans-6-(2,4-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyranYield 81.8%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 24813Phosphorus oxychlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.34 g of 2-tosyloxymethyl-3,4-dihydro-2H-pyran in 25 ml of diethyl ether were added 1.06 g of 2,4-dichlorobenzyl alcohol, followed by a catalytic amount (2-3 drops) of phosphorus oxytrichloride. The mixture was then stirred at room temperature for 4 days, after which 3 drops of triethylamine were added to the mixture, which was then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel as in Example 1(a), to give 1.82 g of trans-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran (having the lesser polarity), 144 mg of cis-6-(2,4-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran (having the greater polarity) and 200 mg of a cis/trans mixture.

Workup

  1. concentrationwas then concentrated by evaporation under reduced pressure
  2. customThe residue was purified by column chromatography through silica gel as in Example 1(a)

Sources & evidence

ORD record
ord-963b87fab3af4ff0bf5eb899ec0cab23
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Linked notes

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