HCID 69828648, compound → HCID 69827849, compound

HRID 1839256Notes

Reaction equation

HRID 1839256 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]#[C:14][CH:15]([OH:18])[CH2:16][CH3:17])[O:4]1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C@H:3]1[C@@H:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][C@@H:6]2[C@@H:5]([C:13]#[C:14][C:15](=[O:18])[CH2:16][CH3:17])[O:4]1

Participants

4

Reactant 1

HCID 69828648HCID 69828648, compound

Product 1

HCID 69827849HCID 69827849, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pent-1-yn-3-ol (1.3 g) in dichloromethane (100 ml) was added to a stirred suspension of manganese dioxide (60 g) in dichloromethane at 0° C. The mixture was stirred at 0° C. for 3 h, filtered through magnesium sulphate (50 g) and the solvent removed in vacuo to give the title compound as a colourless oil (550 mg).

Workup

  1. filtrationfiltered through magnesium sulphate (50 g)
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b582688c07424e02a65c94b66b368c63
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

Loading…