Bromoform → 2-Methoxy-2-(4-morpholinophenyl)acetic acid

HRID 56486

반응식

HRID 56486 반응식
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-:15].[K+].[CH:17](Br)(Br)Br.[OH-:21].[K+].[CH3:23][OH:24]>CO.O1CCOCC1>[CH3:17][O:15][CH:11]([C:10]1[CH:13]=[CH:14][C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:8][CH:9]=1)[C:23]([OH:24])=[O:21]

참가 물질

7

반응물 4

HCID 5558BromoformHCID 14797Potassium HydroxideHCID 2913494-MorpholinobenzaldehydeHCID 23689386Potassium hydroxide methanol

생성물 1

HCID 584321092-Methoxy-2-(4-morpholinophenyl)acetic acid수율 58%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 312751,4-Dioxane용매

실험 절차

An oven-dried flask was charged with 4-(4-morpholinyl)benzaldehyde (10.1 g, 53 mmol), anhydrous methanol (60 mL) and anhydrous dioxane (60 mL) then fitted with an addition funnel. The addition funnel was charged with a solution of KOH (14.8 g, 264 mmol) in anhydrous methanol (60 mL) and an aliquot (˜2 mL) was added to the reaction mixture. Bromoform (5.8 mL, 67.1 mmol) was added to the reaction mixture then the remaining KOH/MeOH solution was added dropwise over 10 minutes. After stirring for 18 h, the mixture was filtered through Celite and rinsed with methanol. The filtrate was collected and concentrated in vacuo. The residue was then diluted with saturated aqueous NH4Cl and extracted with EtOAc. Additional EtOAc was then used to extract the aqueous phase while slowly adjusting the pH from ˜8 to ˜2 using concentrated HCl. A total of approximately 1.5 L of EtOAc was used for the extraction process. The combined EtOAc extracts were dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo gave 2-methoxy-2-(4-morpholinophenyl)acetic acid as a tan solid (7.25 g, 58%).

후처리

  1. customthen fitted with an addition funnel
  2. additionan aliquot (˜2 mL) was added to the reaction mixture
  3. filtrationthe mixture was filtered through Celite
  4. washrinsed with methanol
  5. customThe filtrate was collected
  6. concentrationconcentrated in vacuo
  7. additionThe residue was then diluted with saturated aqueous NH4Cl
  8. extractionextracted with EtOAc
  9. extractionto extract the aqueous phase
  10. dry with materialThe combined EtOAc extracts were dried over Na2SO4
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-1e52a94da63c4f9db6dad8d67985954b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434707B2

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