反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]([CH3:19])([CH3:18])[CH2:7][CH2:6][C:5]2([CH3:21])[CH3:20].C([Li])(C)(C)C.[C:27](=[O:29])=[O:28].Cl>O1CCCC1.CCCCC>[CH2:12]([C:11]1[C:2]([C:27]([OH:29])=[O:28])=[CH:3][C:4]2[C:5]([CH3:20])([CH3:21])[CH2:6][CH2:7][C:8]([CH3:19])([CH3:18])[C:9]=2[CH:10]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- -78 °C
実験手順
15 g of 6-bromo-7-hexyl-1,1,4,4-tetramethyl-1, 2,3,4-tetrahydro-naphthalene were dissolved in 180 ml of tetrahydrofuran and treated dropwise at -78° C. with 64.5 ml of a 1.5 molar solution of tert.butyl-lithium in pentane. After stirring at -78° C. for 1 hour, a carbon dioxide stream was conducted vigorously into the reaction vessel for 2 hours. Subsequently, the reaction mixture was acidified by the addition of 190 ml of 2N hydrochloric acid, extracted several times with ethyl acetate, washed with water, dried over sodium sulfate and evaporated. The oily crude product was filtered over silica gel (eluent hexane, then hexane/ethyl acetate=4:1) and recrystallized from hexane. There were obtained 7.6 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid in colorless crystals, m.p. 98°-99° C.
後処理
- extractionextracted several times with ethyl acetate
- washwashed with water
- dry with materialdried over sodium sulfate
- customevaporated
- filtrationThe oily crude product was filtered over silica gel (eluent hexane
- customhexane/ethyl acetate=4:1) and recrystallized from hexane
出典と根拠
- ORDレコード
- ord-4d21f97b1712426ea5d91e06fbf86981
- 出典データセット
- uspto-grants-1998_03
- 特許番号
- US05726191
関連ノート
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