1,4-Dioxane → (2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7869ノート

反応式

HRID 7869 の反応式
[CH2:1]([CH:4]1[C:16](=[O:17])[C:15]([CH3:18])=[C:14]2[C:6]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:7][C:8]3[C:13]2=[CH:12][CH:11]=[C:10]([O:19][CH2:20][O:21][CH3:22])[CH:9]=3)[CH2:5]1)C=C.[O:27]1[CH2:32][CH2:31][O:30]CC1>O>[CH2:23]([C:6]12[CH2:5][CH:4]([CH2:1][C:31](=[O:30])[CH2:32][OH:27])[C:16](=[O:17])[C:15]([CH3:18])=[C:14]1[C:13]1[C:8](=[CH:9][C:10]([O:19][CH2:20][O:21][CH3:22])=[CH:11][CH:12]=1)[CH2:7]2)[CH2:24][CH2:25][CH3:26]

参加物

4

反応物 2

HCID 312751,4-DioxaneHCID 67401390(2SR,9aSR)-2-allyl-9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 67398080(2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of (2SR,9aSR)-2-allyl-9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (170 mg, 0.48 mmol) in dioxane (9 mL) was diluted with water (3 mL) and treated with a single crystal of OSO4 followed by NaIO4 (125 mg, 0.58 mmol). The mixture was stirred at room temperature for 15 minutes, treated with more NaIO4 (132 mg, 0.62 mmol), and stirred an additional 30 minutes at room temperature. Workup provided a gum which was purified by PLC on two 0.1×20×20 cm silica gel GF plates, developing twice with 4:1 hexanes-EtOAc. The minor UV visible band provided (2RS,9aSR)-9a-butyl-2-(3-hydroxy-2-oxopropyl)-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (26 mg) as an oil. The major UV visible band afforded (2RS,9aSR)-9a-butyl-7-methoxymethoxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (85 mg) as an oil.

後処理

  1. additiontreated with a single crystal of OSO4
  2. stirringstirred an additional 30 minutes at room temperature
  3. customWorkup provided a gum which
  4. customwas purified by PLC on two 0.1×20×20 cm silica gel GF plates

出典と根拠

ORDレコード
ord-30c070b61f1b4129a0cb3214237639c6
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

反応ノート

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