Sulfuric Acid → HCID 22045514、化合物

HRID 1830485ノート

反応式

HRID 1830485 の反応式
[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:15])[CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[OH:16].[H][H].S(=O)(=O)(O)O>[C].[Pd].[O-2].[O-2].[O-2].[Cr+6].O>[CH2:10]1[C:11]2[C:6](=[C:5]3[C:14](=[CH:13][CH:12]=2)[CH2:1][C:2](=[O:16])[CH2:3][CH2:4]3)[CH2:7][CH2:8][C:9]1=[O:15]

参加物

7

反応物 3

HCID 1118Sulfuric AcidHCID 17607477Phenanthrene-2,7-diolHCID 178418361HCID 178418361、化合物

生成物 1

HCID 22045514HCID 22045514、化合物

試薬・触媒・溶媒 3

HCID 10219390chromium (VI) trioxide触媒HCID 178418390HCID 178418390、化合物触媒HCID 962Water溶媒

実験手順

Phenanthren-2,7-diol was reduced with hydrogen in the presence of a 5% palladium-carbon (wet) catalyst, and then oxidized using a mixture of chromium trioxide, sulfuric acid and water to yield 1,3,4,5,6,8-hexahydrophenanthren-2,7-dione. One of the carbonyl groups of this compound was protected with an ethylene glycol, and the compound was then reacted with propylmagnesium bromide, dehydrated in the presence of an acid catalyst, and the partially deprotected group reformed to yield 7-propyl-3, 4,5,6-tetrahydro-1H-phenanthren-2-one ethylene acetal. This compound was then reduced with hydrogen in the presence of a 5% palladium-carbon (wet) catalyst, and then isomerized using potassium-t-butoxide in DMF to yield trans-7-propyl-3,4,5,6,7,8-tetrahydro-1H-phenanthren-2-one. This compound was reacted in the same manner as that described in Example 17 to Example 22, and yielded the compounds listed below.

出典と根拠

ORDレコード
ord-ac7f6a188b224cb29751285da0f33f26
出典データセット
uspto-grants-2006_06
特許番号
US07067179B1

反応ノート

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