Water → 9,10-Dihydrophenanthrene-1-methanol

HRID 1388816ノート

反応式

HRID 1388816 の反応式
[C:1]1([C:15](OCC)=[O:16])[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[C:1]1([CH2:15][OH:16])[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 13281335Ethyl 9,10-dihydrophenanthrene-1-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 132813369,10-Dihydrophenanthrene-1-methanol収率 35.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

Under a dry nitrogen atmosphere a solution of ethyl 9,10-dihydrophenanthrene-1-carboxylate (5.15 grams, 0.02 mole) in anhydrous diethyl ether (50 ml) was added to a slurry of lithium aluminum hydride (0.5 grams, 0.013 mole) in anhydrous diethyl ether (100 ml). The rate was such that a reflux was maintained throughout the addition. After complete addition, the mixture was stirred at room temperature for two hours. Water (1 ml) was cautiously added to the reaction mixture, followed by 10% aqueous sodium hydroxide (1 ml) and water (3 ml). Diatomaceous earth was added to the mixture and the resultant mixture filtered. The filter cake was washed with diethyl ether and the filtrates combined and evaporated under reduced pressure to give a green solid. This solid was chromatographed on silica gel using methylene chloride as eluant to give a brown solid. Recrystallization from n-hexane gave 9,10-dihydrophenanthrene-1-methanol (1.5 grams) as tan crystals (mp 108°-110°).

後処理

  1. temperaturewas maintained throughout the addition
  2. additionAfter complete addition
  3. additionDiatomaceous earth was added to the mixture
  4. filtrationthe resultant mixture filtered
  5. washThe filter cake was washed with diethyl ether
  6. customevaporated under reduced pressure
  7. customto give a green solid
  8. customThis solid was chromatographed on silica gel
  9. customto give a brown solid
  10. customRecrystallization from n-hexane

出典と根拠

ORDレコード
ord-48e6ad2125574580817a9bed3b61dab1
出典データセット
uspto-grants-1984_02
特許番号
US04433182

反応ノート

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