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

HRID 640511

반응식

HRID 640511 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-c41d5c019f8746b5a0c78ecc72fd2aba
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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