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

HRID 78228

반응식

HRID 78228 반응식
[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]

참가 물질

7

반응물 4

HCID 8028Tetrahydrofuran2회HCID 20417N-FormylmorpholineHCID 219386012-(4-Bromo-2-Fluorophenyl)-1,3-DioxolaneHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3fd21338916e49338a64aa7534abcedc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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