N-Formylmorpholine → 4-(Phenoxymethyl)benzaldehyde

HRID 1691156

반응식

HRID 1691156 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C([Li])CCC.[CH:21](N1CCOCC1)=[O:22]>O1CCCC1>[O:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:21]=[O:22])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 20417N-FormylmorpholineHCID 7261491-Bromo-4-(phenoxymethyl)benzeneHCID 178418339Butyllithium

생성물 1

HCID 121062874-(Phenoxymethyl)benzaldehyde수율 100.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
78 °C

실험 절차

To a tetrahydrofuran solution (50 mL) of 1-bromo-4-phenoxymethyl-benzene (4.69 g, 17.8 mmol) described in Manufacturing Example 86-1-1 was added dropwise n-butyl lithium (16.8 mL, 1.59 M hexane solution, 26.7 mmol) at −78° C. After 40 minutes of stirring at 78° C., N-formylmorpholine (2.25 g, 19.6 mmol) was added to this mixture, which was then stirred for a further 30 minutes at that temperature. This mixture was partitioned into diethyl ether and water. 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 (3.8 g). This compound was used in the subsequent reaction without purification.

후처리

  1. stirringwas then stirred for a further 30 minutes at that temperature
  2. customThis mixture was partitioned into diethyl ether and water
  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-7d7ef1525c574f3aa00d4ad7c2e772a9
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

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