HCID 11586634, compound → HCID 11528683, compound

HRID 2053401Notes

Reaction equation

HRID 2053401 reaction equation
[CH3:1][C@H:2]([CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:3][C:4]#[C:5][CH:6]([OH:8])[CH3:7]>C1COCC1.[O-2].[O-2].[Mn+4]>[CH3:1][C@H:2]([CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:3][C:4]#[C:5][C:6](=[O:8])[CH3:7]

Participants

4

Reactant 1

HCID 11586634HCID 11586634, compound

Product 1

HCID 11528683HCID 11528683, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 300 g (1.3255 mol) solution of (2RS,6S)-6-methyl-7-[(RS)-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxy]hept-3-in-2-ol, dissolved in 600 ml of THF, is added by stirring to a suspension of 1500 g manganese dioxide in 2250 ml of THF, and stirring is continued at room temperature for 48 hours. The suspension is then filtered over silica gel and the solvent is removed in vacuo. 280 g of the product is obtained.

Workup

  1. additionis added
  2. filtrationThe suspension is then filtered over silica gel
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5d2de440f4934a1c861e482e9594be9f
Source dataset
uspto-grants-2008_02
Patent number
US07326798B2

Reaction notes

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