Dichloromethane → 3-((Tert-butyldimethylsilyl)oxy)propanal

HRID 1453639Notes

Reaction equation

HRID 1453639 reaction equation
C(Cl)Cl.[Si:4]([O:11][CH2:12][CH2:13][CH2:14][OH:15])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(#N)C>[Si:4]([O:11][CH2:12][CH2:13][CH:14]=[O:15])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

Product 1

HCID 36623923-((Tert-butyldimethylsilyl)oxy)propanalYield 69,024.297%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

Tetrapropylammonium perruthenate (0.18 g, 5.3 mmol) was added to a mixture of methylene chloride (20 mL) and acetonitrile (2 mL) containing 3-(tert-butyldimethylsilyloxy)-propanol (2 g, 0.01 mmol), N-methylmorpholine N-oxide (1.76 g) and 4 Å molecular sieves. The reaction mixture was stirred at RT overnight and then filtered through a pad of silica gel. The filtrate was concentrated under vacuo to afford 3-(tert-butyldimethylsilyloxy)-propionaldehyde (1.3 g, 66%).

Workup

  1. filtrationfiltered through a pad of silica gel
  2. concentrationThe filtrate was concentrated under vacuo

Sources & evidence

ORD record
ord-81f3e1a46fd44b17a0bd3a3b063a5631
Source dataset
uspto-grants-2009_01
Patent number
US07476676B2

Reaction notes

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