Ammonium cerium-nitrate → (S)-(+)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethyl-p-benzoquinone

HRID 224735

反応式

HRID 224735 の反応式
[N+]([O-])([O-])=[O:2].[NH4+].[Ce].CO[C:9]1([CH3:29])[C:14]([CH3:15])=[C:13]([O:16]C)[C:12]([CH3:18])=[C:11]([CH2:19][CH2:20][C@@:21]2([CH3:28])[CH2:25][O:24]C(C)(C)[O:22]2)[CH2:10]1>O.C(#N)C>[OH:22][C@:21]([CH3:28])([CH2:25][OH:24])[CH2:20][CH2:19][C:11]1[C:10](=[O:2])[C:9]([CH3:29])=[C:14]([CH3:15])[C:13](=[O:16])[C:12]=1[CH3:18]

参加物

5

反応物 2

HCID 57418452Ammonium cerium-nitrateHCID 70593036(S)-4-(3,5-dimethoxy-3,4,6-trimethyl-phenylethyl)-2,2,4-trimethyl-1,3-dioxolan

生成物 1

HCID 13100536(S)-(+)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethyl-p-benzoquinone収率 41.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

While stirring for 2 minutes at room temperature, 2.01 g of cerium ammonium nitrate in 7.5 ml of water were added dropwise to a solution of 550 mg of (S)-4-(3,5-dimethoxy-3,4,6-trimethyl-phenylethyl)-2,2,4-trimethyl-1,3-dioxolan in 7.5 ml of acetonitrile. After 2 minutes of additional stirring, the reaction mixture was extracted three times with 20 ml of chloroform each time. The combined organic extracts were dried over sodium sulfate, whereafter the solvent was removed. After chromatography of the obtained residue on silica gel with benzene/ethyl acetate (2:1 parts by volume) and ethyl acetate, there were obtained 266 mg of (S)-(+)-2,3,6-trimethyl-5-(2,2,4-trimethyl-1,3-dioxolan-4-ethyl)-p-benzoquinone and 177 mg of (S)-(+)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethyl-p-benzoquinone in the form of yellow needles with a melting point of 111°-112°.

後処理

  1. waitAfter 2 minutes of additional stirring
  2. extractionthe reaction mixture was extracted three times with 20 ml of chloroform each time
  3. dry with materialThe combined organic extracts were dried over sodium sulfate, whereafter the solvent
  4. customwas removed

出典と根拠

ORDレコード
ord-12f2e00f35a244c6bc18dd4018a4c9b1
出典データセット
uspto-grants-1980_11
特許番号
US04234490

関連ノート

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