Methyl morpholine oxide → 2-t-Butyldiphenylsilyloxymethyl-2-propenal

HRID 398767

Reaction equation

HRID 398767 reaction equation
[Si:1]([O:18][CH2:19][C:20](=[CH2:23])[CH2:21][OH:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Si:1]([O:18][CH2:19][C:20](=[CH2:23])[CH:21]=[O:22])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 114502322-t-Butyldiphenylsilyloxymethyl-2-propene-1-ol

Product 1

HCID 533097872-t-Butyldiphenylsilyloxymethyl-2-propenalYield 83%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 2-t-butyldiphenylsilyloxymethyl-2-propene-1-ol (25.5 g, 86.7 mmol), molecular sieves in powder (26 g), N-methylmorpholine-N-oxide (15.3 g, 130 mmol) and tetrapropylammoniumperruthenate (1.5 g, 4 mmol) in anhydrous dichloromethane (400 ml) is stirred overnight at 20° C. Then the reaction mixture is concentrated in vacuo and purified by flash chromatography on silica gel to give the title product (21 g, 83%).

Workup

  1. concentrationThen the reaction mixture is concentrated in vacuo
  2. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8661d624be634f08924ce746aaf0c6dc
Source dataset
uspto-grants-1998_10
Patent number
US05817647

Linked notes

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