22348-97-6 Usage
Synthesis
The carboxylic acid (13.8 g, 69 mmol, 1.0 equivalents) was dissolved in dry THF under an inert atmosphere and cooled to 0 oC. CDI (13.4 g, 83 mmol, 1.2 equivalents) was then added in small portions over several minutes. After 10 min, the reaction was allowed to warm slowly to room temperature and was then stirred for 1 h. In a separate flflask, monomethyl malonate (9.8g, 83 mmol, 1.2 equivalents) was dissolved in THF under an inert atmosphere and cooled to ?78 oC. To this solution was added dibutylmagnesium (1.0 M in heptane, 0.6 equivalents). A white solid formed instantly on addition of the base. After 10 min, the reaction was warmed to room temperature and stirred for 1 h. The acylimidazole was then added by cannula to the flflask containing the magnesium salt. The resulting slurry was stirred for ?3 days. The reaction mixture was then concentrated on a rotary evaporator and the residue redissolved in EtOAc. The resulting solution was washed with 1.2 M HCl, saturated aqueous NaHCO3, and brine. The organic phase was dried over sodium sulfate, fifiltered, concentrated, and the residue purifified by flflash chromatography (7:1 hexanes:EtOAc) to give the β-keto ester (14.7g, 83%).Reference: Durham, T. B.; Miller, M. J. J. Org. Chem. 2003, 68, 27–34.
Chemical Properties
Yellow Crystalline Solid
Uses
Methyl 3-Oxotetradecanoate (cas# 22348-97-6) is a compound useful in organic synthesis.
Check Digit Verification of cas no
The CAS Registry Mumber 22348-97-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,3,4 and 8 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 22348-97:
(7*2)+(6*2)+(5*3)+(4*4)+(3*8)+(2*9)+(1*7)=106
106 % 10 = 6
So 22348-97-6 is a valid CAS Registry Number.
InChI:InChI=1/C15H28O3/c1-3-4-5-6-7-8-9-10-11-12-14(16)13-15(17)18-2/h3-13H2,1-2H3
22348-97-6Relevant articles and documents
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Viscontini,Merckling
, p. 2280 (1952)
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Intermediate, synthesis and application of vaccine adjuvant MPLA
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Paragraph 0100-0106, (2021/10/27)
The invention discloses an intermediate of a vaccine adjuvant MPLA, and synthesis and application thereof. The intermediate provided by the invention takes the allyl phosphate ligand as MPLA phosphate group source, Nap is a protecting group, and can be conveniently removed in subsequent operation. The synthesized intermediate route is short, and the total yield is obviously increased. For synthesis and amplification MPLA, a foundation is provided.
Intermediate, synthesis and application of vaccine adjuvant MPLA
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Paragraph 0121-0124, (2021/10/27)
The invention discloses an intermediate of a vaccine adjuvant MPLA, and synthesis and application thereof. The intermediate provided by the invention uses Nap as a protecting group, and can be conveniently removed in subsequent operation. The synthesis route is short, and the total yield is obviously increased. For synthesis and amplification MPLA, a foundation is provided.
