Diethyl Ether → 1-(2,2,3,4,6,7-Hexamethyl-3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine

HRID 1850402노트

반응식

HRID 1850402 반응식
[CH2:1](OCC)C.C[Li].O1CCCC1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]3[C:28]([CH3:41])=[C:29]([CH3:40])[C:30]4[O:34][C:33]([CH3:36])([CH3:35])[C:32](=[O:37])[C:31]=4[C:38]=3[CH3:39])[CH2:23][CH2:22]2)=[CH:17][CH:16]=1>C(OCC)(=O)C.O>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH2:22][CH2:23][N:24]([C:27]3[C:28]([CH3:41])=[C:29]([CH3:40])[C:30]4[O:34][C:33]([CH3:36])([CH3:35])[C:32]([CH3:1])([OH:37])[C:31]=4[C:38]=3[CH3:39])[CH2:25][CH2:26]2)=[CH:19][CH:20]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 229355955-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-oneHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 229356081-(2,2,3,4,6,7-Hexamethyl-3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine수율 96.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A diethylether solution (5.60 mL, 6.38 mmol) containing 1.14 M methyl lithium was added dropwise to a solution of tetrahydrofuran (20 mL) containing 5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one (2.00 g, 5.06 mmol) synthesized in Reference Example 42 under ice-cooling condition, and the mixture was stirred for 10 minutes. Water was added to the reaction solution, and extraction was performed using ethyl acetate. The organic layer was washed with water and saturated saline, and then dried using anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the obtained residue was crystallized using hexane to give 2.00 g of the title compound (yield: 96%).

후처리

  1. customsynthesized in Reference Example 42 under ice-
  2. temperaturecooling condition
  3. washThe organic layer was washed with water and saturated saline
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was crystallized

출처 및 근거

ORD 기록
ord-240b0de74ec547e7b21ca45553556862
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957069B2

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