Ammonium Chloride → 9-Benzyl-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol

HRID 1485085

反応式

HRID 1485085 の反応式
[CH3:1][C:2]1([CH3:14])[CH2:13][O:12][C:5]2([CH2:11][CH2:10][C:8](=[O:9])[CH2:7][CH2:6]2)[O:4][CH2:3]1.[Cl-].[NH4+].[CH2:17]([Mg]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[CH2:17]([C:8]1([OH:9])[CH2:7][CH2:6][C:5]2([O:4][CH2:3][C:2]([CH3:14])([CH3:1])[CH2:13][O:12]2)[CH2:11][CH2:10]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 5879683,3-Dimethyl-1,5-dioxaspiro(5.5)undecan-9-oneHCID 178419663HCID 178419663、化合物

生成物 1

HCID 1181131779-Benzyl-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1,4-cyclohexanedione mono-2,2-dimethyltrimethylene ketal (3.76 g) and zinc chloride (about 1.0 mol/L, solution in diethyl ether, 1.90 mL) in tetrahydrofuran (63.0 mL), benzylmagnesium bromide (about 1.0 mol/L, solution in tetrahydrofuran, 24.7 mL) was added at 0° C. and thereafter the mixture was stirred at that temperature for 2.5 hours. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added and three extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine and thereafter dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-60:40) to give 9-benzyl-3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol as a colorless solid (1.28 g).

後処理

  1. extractionthree extractions
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-60:40)

出典と根拠

ORDレコード
ord-cf3c8959c6b94260993dd2e3d49cdada
出典データセット
uspto-grants-2016_08
特許番号
US09422240B2

関連ノート

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