Tetrahydrofuran → 4-[1,3]Dioxolan-2-yl-3-fluoro-benzaldehyde

HRID 1691334

反応式

HRID 1691334 の反応式
[O:1]1CCC[CH2:2]1.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[C:9]([F:18])[CH:8]=1.C([Li])CCC.C(N1CCOCC1)=O>C(OCC)(=O)C.O>[O:14]1[CH2:15][CH2:16][O:17][CH:13]1[C:10]1[CH:11]=[CH:12][C:7]([CH:2]=[O:1])=[CH:8][C:9]=1[F:18]

参加物

7

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 20417N-FormylmorpholineHCID 219386012-(4-Bromo-2-Fluorophenyl)-1,3-DioxolaneHCID 178418339Butyllithium

生成物 1

HCID 592554594-[1,3]Dioxolan-2-yl-3-fluoro-benzaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

To a tetrahydrofuran (600 mL) solution of 2-(4-bromo-2-fluoro-phenyl)-[1,3]dioxolane (12.5 g, 50.7 mmol) described in Manufacturing Example 204-1-1 was added dropwise n-butyl lithium (28.5 mL, 2.67 M hexane solution, 76.1 mmol) over 15 minute. The system was stirred for 5 minutes at −78° C., after which a THF solution of N-formylmorpholine (5.61 mL, 55.8 mmol) was added to this reaction solution, which was stirred for another 2.5 hours at room temperature. Water and ethyl acetate were added to this mixture, which was partitioned. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (9.99 g). The title compound was used in the following reaction without any further purification.

後処理

  1. stirringwas stirred for another 2.5 hours at room temperature
  2. customwas partitioned
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure

出典と根拠

ORDレコード
ord-fe83de106c7f4d8cabd18a04ef7d6764
出典データセット
uspto-grants-2012_04
特許番号
US08153662B2

関連ノート

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