Dodecanoyl chloride → HCID 19385056, compound

HRID 2399905Notes

Reaction equation

HRID 2399905 reaction equation
[CH3:1][Si:2]([CH3:18])([CH3:17])[C:3]1[O:7][C:6]([CH3:8])=[C:5]([CH2:9][OH:10])[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:19](Cl)(=[O:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C(N(CC)CC)C>[CH3:18][Si:2]([CH3:17])([CH3:1])[C:3]1[O:7][C:6]([CH3:8])=[C:5]([CH2:9][O:10][C:19](=[O:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8166Dodecanoyl chlorideHCID 15744588HCID 15744588, compound2×

Product 1

HCID 19385056HCID 19385056, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Phenyl-5-trimethylsilyl-3-furancarboxaldehyde (Compound 12) is reduced with lithium aluminum hydride to yield the corresponding alcohol (Compound 13), which is thereafter methylated with methyl iodide in the presence of n butyl lithium and lithium chloride in the 5-position of the furan nucleus to yield 5-trimethylsilyl-4-phenyl-3-hydroxymethyl-2-methylfuran (Compound 14). 5-Trimethylsilyl-4-phenyl-3-hydroxymethyl-2-methylfuran (Compound 14) is esterified by treatment with lauroyl chloride in the presence of triethylamine to yield 5-trimethylsilyl-4-phenyl-3-dodecoyloxymethyl-2-methylfuran (Compound 15). Compound 15 is subjected to singlet oxidation, in a chilled (approximately -5° C.) dry tetrahydrofuran solution, in the presence of Rose Bengal dye under irradiation with light to provide 4-dodecoyloxymethyl-5-hydroxy-5-methyl-3-phenyl-2-furanone (Compound 5).

Sources & evidence

ORD record
ord-c31e1241f2994b3fa3262363fe708220
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

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