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

HRID 272768

反応式

HRID 272768 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-14d67ec816ab498c8fe3a222b5ca4a1f
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

関連ノート

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