Sodium hydride → 4-{4-[2-(Tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-morpholine

HRID 272768

반응식

HRID 272768 반응식
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:17][CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1>CN(C=O)C>[O:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH:20]1[O:19][CH2:18][CH2:17][O:13][C:10]1[CH:9]=[CH:8][C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 805104-MorpholinophenolHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

생성물 1

HCID 692191944-{4-[2-(Tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-morpholine수율 78.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

4-morpholinophenol (0.358 g, 2 mmol) in DMF (5 mL) was cooled to 0° C. To this solution was added 60% NaH (0.192 g, 4.8 mmol). After the bubbling ceased, 2-(2-bromo-ethoxy)-tetrahydro-pyran (0.501 g, 2.4 mmol) in DMF (2 mL) was added to the above solution. The solution was stirred at room temperature for 2 hours, and partitioned between EtOAc and water. The aqueous layer was extracted with additional EtOAc, and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 7:3 hexanes/EtOAc to give 0.48 g of the title compound (78%).

후처리

  1. custompartitioned between EtOAc and water
  2. extractionThe aqueous layer was extracted with additional EtOAc
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 7:3 hexanes/EtOAc

출처 및 근거

ORD 기록
ord-14d67ec816ab498c8fe3a222b5ca4a1f
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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