2-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol → 2-({[tert-Butyl(dimethyl)silyl]oxy}methyl)prop-2-enal

HRID 627181Notes

Reaction equation

HRID 627181 reaction equation
[Si:1]([O:8][CH2:9][C:10](=[CH2:13])[CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4].O=[Mn]=O>[Si:1]([O:8][CH2:9][C:10](=[CH2:13])[CH:11]=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 112064702-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol2×

Product 1

HCID 574134022-({[tert-Butyl(dimethyl)silyl]oxy}methyl)prop-2-enalYield 59.6%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(((tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol (Intermediate 157, 11.35 g, 56.09 mmol) in DCM (150 mL) was added manganese dioxide (activated, 5 g) (28.7 g, 280.43 mmol). The reaction mixture was stirred at room temperature for three days. More MnO2 was added and continued stirring until TLC shows minimum starting material. The reaction mixture was filtered through a pad of silica, evaporated at ˜15° C. and purified on silica gel column (5-20%, EA/Hex) to afford the title compound (6.70 g, 59.6%) as a colorless oil.

Workup

  1. stirringcontinued stirring until TLC
  2. filtrationThe reaction mixture was filtered through a pad of silica
  3. customevaporated at ˜15° C.
  4. custompurified on silica gel column (5-20%, EA/Hex)

Sources & evidence

ORD record
ord-708cd8e1a70f4199be4077c22934390e
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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