HCID 67396734, compound → HCID 67398277, compound

HRID 1990707Notes

Reaction equation

HRID 1990707 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:21])[C:9]#[C:10][CH2:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:21])[C:9]#[C:10][CH2:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67396734HCID 67396734, compound

Product 1

HCID 67398277HCID 67398277, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 16.60 g (53.7 mmol) of 1-(4-chlorophenyl)-6-(tetrahydro-2H-pyran-2-yloxy)hex-2-yn-1-ol, prepared in stage 5.1., is added dropwise to a suspension, cooled with an ice bath, of 93 g (1.07 mol) of manganese dioxide in 500 ml of dichloromethane. Stirring is continued for 1.5 hours, then the mixture is filtered through celite and the filter cake is rinsed with dichloromethane. The filtrates are evaporated to produce 16.3 g (53.1 mmol) of product in the form of a yellowish oil.

Workup

  1. addition, is added dropwise to a suspension
  2. filtrationthe mixture is filtered through celite
  3. washthe filter cake is rinsed with dichloromethane
  4. customThe filtrates are evaporated

Sources & evidence

ORD record
ord-ee96f29de09147b6ba380cc5bb66c98e
Source dataset
uspto-grants-2010_01
Patent number
US07645757B2

Reaction notes

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