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Benzenemethanol, 2,6-dichloro- → trans-6-(2,6-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran

HRID 905058
Notes
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Reaction equation

HRID 905058 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]=[CH:26][CH:25]=[C:24]([Cl:28])[C:21]=1[CH2:22][OH:23]>C(OCC)C.O=P(Cl)(Cl)Cl>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27156Benzenemethanol, 2,6-dichloro-HCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 54030357trans-6-(2,6-Dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyranYield 71.1%

Reagents, catalysts & solvents 2

HCID 24813Phosphorus oxychlorideCatalystHCID 3283
Diethyl Ether
Solvent

Procedure

To a solution of 1.34 g of 2-tosyloxymethyl-3,4-dihydro-2H-pyran and 1.06 g of 2,6-dichlorobenzyl alcohol in 25 ml of diethyl ether was added a catalytic amount (2 drops) of phosphorus oxytrichloride, and then the mixture was stirred at room temperature for 4 days. The colourless crystals which had precipitated were filtered off, giving 1.582 g of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran, melting at 123°-124° C. Triethylamine was then added to the mother liquor and the resulting mixture was evaporated under reduced pressure and the residue purified by column chromatography through silica gel, in essentially the same manner as described in Example 1(a), to give 338 mg of trans-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran and 306 mg of cis-6-(2,6-dichlorobenzyloxy)-2-tosyloxymethyltetrahydropyran.

Workup

  1. customThe colourless crystals which had precipitated
  2. filtrationwere filtered off

Sources & evidence

ORD record
ord-89332c3cc6314095a42f066bc7580a28
Source dataset
uspto-grants-1983_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04421758

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes