1,3-Propanediol → HCID 23249714, compound

HRID 1274483Notes

Reaction equation

HRID 1274483 reaction equation
[Si](O[CH2:9][CH2:10][CH:11]=[O:12])(C(C)(C)C)(C)C.[CH2:13]([OH:17])[CH2:14][CH2:15][OH:16].[Si](OCCCO)([C:21](C)([CH3:23])[CH3:22])(C)C.[CH3:30]S(C)=O.[C:34](Cl)(=O)[C:35](Cl)=O>>[CH3:22][C:21]1([CH3:23])[O:17][CH:13]([C:10]([CH3:9])([C:11](=[O:12])[CH2:34][CH3:35])[CH3:30])[CH2:14][CH2:15][O:16]1

Participants

5

Reactant 4

HCID 104421,3-PropanediolHCID 36623923-((Tert-butyldimethylsilyl)oxy)propanal2×HCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-olHCID 13524712HCID 13524712, compound

Product 1

HCID 23249714HCID 23249714, compound

Procedure

3-[(tert-Butyldimethylsilyl)oxy]propanal 42 is produced using propane-1,3-diol 40 as a starting material by monosilylation into 3-[(tert-butyldimethylsilyl)oxy]-1-propanol 41 being done first according to a method of P. G. McDougal, J. G. Rico, Y. Oh, B. D. Condon, J. Org. Chem. 1986, 51, 3388-3390, which then is oxidized to aldehyde 42 with DMSO/oxalyl chloride (A. Jenmalm, W. Berts, Y. Li, K. Luthmann, I. Csoregh, U. Hacksell, J. Org. Chem. 1994, 59, 1139-1148).

Sources & evidence

ORD record
ord-b515d3e2cfc34b9c980f661ed32e9ce0
Source dataset
uspto-grants-2000_12
Patent number
US06156905

Reaction notes

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