1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → 2-((Tert-butyldimethylsilyl)oxy)acetaldehyde

HRID 353381Notes

Reaction equation

HRID 353381 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC1(C)N(O)C(C)(C)CC(O)C1>C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanol

Product 1

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Solution 1 consisted of 108 g (0.610 mol) of 2-(tert-butyldimethylsilyloxy)ethanol and 5.8 g of 4-hydroxy-TEMPO in 400 ml of ethyl acetate. Flow rates: 48 l/h for solution 1, 30 l/h for solution 2. tert-Butyldimethylsilyloxyacetaldehyde was isolated by fractional distillation of the ethyl acetate phase. B.p.: 74-80° C. (22 mbar).

Sources & evidence

ORD record
ord-8a6e157a737b4d039d5b66319c432844
Source dataset
uspto-grants-2004_06
Patent number
US06750371B2

Reaction notes

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