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Tetrahydrofuran → {5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methyl methanesulfonate

HRID 1850519
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HRID 1850519 반응식
C1COCC1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:21]([CH3:34])=[C:22]([CH3:33])[C:23]4[O:27][C:26]([CH2:29][OH:30])([CH3:28])[CH2:25][C:24]=4[C:31]=3[CH3:32])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>O.C(OCC)(=O)C>[CH3:42][S:43]([O:30][CH2:29][C:26]1([CH3:28])[CH2:25][C:24]2[C:31]([CH3:32])=[C:20]([N:17]3[CH2:16][CH2:15][N:14]([C:11]4[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=4)[CH2:19][CH2:18]3)[C:21]([CH3:34])=[C:22]([CH3:33])[C:23]=2[O:27]1)(=[O:45])=[O:44]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46910479{5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methanol

생성물 1

HCID 59485125{5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methyl methanesulfonate수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of THF (2.0 mL) containing {5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methanol (200 mg, 0.504 mmol) synthesized in Example 97, triethylamine (102 mg, 1.01 mmol) and methanesulfonyl chloride (87 mg, 0.756 mmol) were serially added under ice-cooling condition, and the mixture was warmed to room temperature and stirred for 15 hours. The reaction solution was diluted with water, and extraction was performed using ethyl acetate. The extract was washed with saturated saline and dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-75:25) to give 220 mg of the title compound (yield: 92%). An amorphous solid.

후처리

  1. additionwere serially added under ice-
  2. temperaturecooling condition
  3. washThe extract was washed with saturated saline
  4. customdried
  5. customAfter that, the solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-75:25)

출처 및 근거

ORD 기록
ord-caf3f91d283a45d8a92eea439c714777
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957069B2

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