Hexane → 4-{1-Ethyl-1-[4-(3-hydroxy-4,4-dimethyl-1-pentynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol

HRID 546810노트

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HRID 546810 반응식
C([Li])CCC.CCCCCC.[CH2:12]([C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([CH3:33])[CH:27]=1)([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[C:19]([CH3:25])[CH:18]=1)[CH2:15][CH3:16])[CH3:13].[CH3:34][C:35]([CH3:39])([CH3:38])[CH:36]=[O:37].[Cl-].[NH4+]>O1CCCC1>[CH2:12]([C:14]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([CH3:33])[CH:27]=1)([C:17]1[CH:22]=[CH:21][C:20]([C:23]#[C:24][CH:36]([OH:37])[C:35]([CH3:39])([CH3:38])[CH3:34])=[C:19]([CH3:25])[CH:18]=1)[CH2:15][CH3:16])[CH3:13]

참가 물질

7

반응물 5

HCID 8058HexaneHCID 12417PivalaldehydeHCID 25517Ammonium ChlorideHCID 585982954-[1-Ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenolHCID 178418339Butyllithium

생성물 1

HCID 574330574-{1-Ethyl-1-[4-(3-hydroxy-4,4-dimethyl-1-pentynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 2.44 M solution of n-butyllithium in hexane (42.8 mL, 104.5 mmol) was added to a solution of 4-[1-ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenol (Example 1-(3); 12.22 g, 41.8 mmol) in tetrahydrofuran (300 mL) at 0° C., and the mixture was stirred at the same temperature for 30 minutes. Trimethylacetaldehyde (13.79 mL, 125.4 mmol) was added at 0° C., and the mixture was stirred at the same temperature for 30 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane/ethyl acetate=9/1 to 3/1) to give the title compound (13.08 g, 83%).

후처리

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a silica gel column (hexane/ethyl acetate=9/1 to 3/1)

출처 및 근거

ORD 기록
ord-91e5fa7a028849898dd68e85c961ec1b
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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