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

HRID 1485085

반응식

HRID 1485085 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cf3c8959c6b94260993dd2e3d49cdada
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422240B2

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