HCID 70511091, compound → HCID 86737361, compound

HRID 1732269Notes

Reaction equation

HRID 1732269 reaction equation
[OH:1][CH:2]1[CH2:8][CH2:7]/[C:6](=[CH:9]\[CH2:10][OH:11])/[CH2:5][O:4][C:3]1([CH2:13][CH2:14][CH2:15][CH:16]([CH3:25])[CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[CH3:12]>[O-2].[O-2].[Mn+4].C(Cl)Cl>[CH3:12][C:3]1([CH2:13][CH2:14][CH2:15][CH:16]([CH3:25])[CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH:2]2[O:1][C:6]([CH2:9][CH:10]=[O:11])([CH2:7][CH2:8]2)[CH2:5][O:4]1

Participants

4

Reactant 1

HCID 70511091HCID 70511091, compound

Product 1

HCID 86737361HCID 86737361, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-[(2RS,3SR)-3-hydroxy-6-[(E)-2-hydroxyethylidene]-2-methyl-2-oxepanyl]-2-methyl-1-(tetrahydropyran-2-yloxy)pentane (953 mg, 2.67 mM), manganese dioxide (4 g) and methylene chloride (20 ml) is stirred for three days at room temperature under nitrogen. The mixture is filtered through a pad of Celite and washed with methylene chloride (2×30 ml). The solvent is removed in vacuo and the residue purified by column chromatography on silica gel (15 g) with 30% ether in petroleum ether to give (1RS,4SR,5RS)-4-methyl-4-[4-methyl-5-(tetrahydropyran-2-yloxy)pentyl]-3,8-dioxabicyclo [3.2.1] octane-1-acetaldehyde (0.813 g, 73%) as a colorless oil.

Workup

  1. filtrationThe mixture is filtered through a pad of Celite
  2. washwashed with methylene chloride (2×30 ml)
  3. customThe solvent is removed in vacuo
  4. customthe residue purified by column chromatography on silica gel (15 g) with 30% ether in petroleum ether

Sources & evidence

ORD record
ord-d87e1a8fea05408f8e051034d4f2988e
Source dataset
uspto-grants-1980_12
Patent number
US04237054

Reaction notes

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