Dimethyl Sulfoxide → 4-(2-Methoxy-4-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

HRID 1443194ノート

反応式

HRID 1443194 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[C:16]([CH3:27])([CH3:26])[CH2:17][C:18]([OH:25])([C:21]([F:24])([F:23])[F:22])[CH2:19][OH:20].C(Cl)(=O)C(Cl)=O.CS(C)=O>C(OCC)C.C(N(CC)CC)C>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[C:16]([CH3:27])([CH3:26])[CH2:17][C:18]([OH:25])([C:21]([F:23])([F:24])[F:22])[CH:19]=[O:20]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 179892434-(2-Methoxy-4-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanolHCID 21226445Aluminium lithium hydride

生成物 1

HCID 179891274-(2-Methoxy-4-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal収率 84.6%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8471Triethylamine溶媒

実験手順

Analogously to Example 7, 4.84 g of 4-(2-methoxy-4-methylphenyl)-4-methyl-2-oxopentanoic acid ethyl ester is reacted with 7 ml of trifluoromethyltrimethylsilane and 3 ml of tetrabutylammonium fluoride solution (1 M in THF) in 56 ml THF to form 4.14 g of 4-(2-methoxy-4-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoic acid ethyl ester. The product is reduced with 856 mg of lithium aluminum hydride in 170 ml of diethyl ether to 3.58 g of 4-(2-methoxy-4-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanol. The oxidation of the diol is carried out analogously to Example 7 under Swern conditions with 1.1 ml of oxalyl chloride, 2.1 ml of DMSO and 8.0 ml of triethylamine to 3.01 g of the title compound.

出典と根拠

ORDレコード
ord-5c73a4dd53a245a98f71251326295d33
出典データセット
uspto-grants-2010_02
特許番号
US07659297B2

反応ノート

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