Hydrochloric Acid → 2,4,4-Trimethyl-3-(15-hydroxypentadecyl)-2-cyclohexen-1-one

HRID 1768450ノート

反応式

HRID 1768450 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][Si](C(C)(C)C)(C)C.[Mg].C([O:28][C:29]1[CH2:34][CH2:33][C:32]([CH3:36])([CH3:35])[C:31](=O)[C:30]=1[CH3:38])C.Cl.C(=O)([O-])O.[Na+]>C(OCC)C.O1CCCC1>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:31]1[C:32]([CH3:36])([CH3:35])[CH2:33][CH2:34][C:29](=[O:28])[C:30]=1[CH3:38]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5462224MagnesiumHCID 205455943-Ethoxy-2,6,6-trimethyl-2-cyclohexen-1-oneHCID 23615174[(15-Bromopentadecyl)oxy](tert-butyl)dimethylsilane

生成物 1

HCID 97991882,4,4-Trimethyl-3-(15-hydroxypentadecyl)-2-cyclohexen-1-one収率 39%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

15-Bromo-1-(t-butyldimethylsiloxy)pentadecane (1 g, 2.36 mmol) dissolved in absolute ethyl ether (3 mL) and magnesium (0.115 g) were mixed, and the mixture was refluxed for 40 minutes. Subsequently, 3-ethoxy-2,6,6-trimethyl-2-cyclohexen-1-one (287.5 mg, 1.57 mmol) dissolved in tetrahydrofuran (2 mL) was added thereto. After stirring the mixture for four hours, 10% hydrochloric acid (3 mL) was added, and the reaction was allowed to continue for a further 17 hours under stirring. The reaction mixture was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl ether three times. The organic layers were combined, washed with aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by means of silica gel column chromatography (hexane/ethyl acetate=9/1-6/4; concentration gradient=5%), to thereby afford 222.7 mg (0.61 mmol) of 3-(15-hydroxypentadecyl)-2,4,4-trimethyl-2-cyclohexen-1-one.

後処理

  1. temperaturethe mixture was refluxed for 40 minutes
  2. additionwas added
  3. waitto continue for a further 17 hours
  4. stirringunder stirring
  5. extractionfollowed by extraction with ethyl ether three times
  6. washwashed with aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by means of silica gel column chromatography (hexane/ethyl acetate=9/1-6/4; concentration gradient=5%)

出典と根拠

ORDレコード
ord-8bbd00907f1c45f0877f2cd092d91d2d
出典データセット
uspto-grants-2007_06
特許番号
US07235700B2

反応ノート

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