Bromoform → 2-Methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetic acid

HRID 56507

반응식

HRID 56507 반응식
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)=[N:4][N:3]=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]([C:5]2[O:6][C:2]([CH3:1])=[N:3][N:4]=2)=[CH:8][CH:9]=1)[C:23]([OH:24])=[O:21]

참가 물질

7

반응물 4

HCID 5558BromoformHCID 14797Potassium HydroxideHCID 106552074-(5-Methyl-1,3,4-oxadiazol-2-yl)benzaldehydeHCID 23689386Potassium hydroxide methanol

생성물 1

HCID 584320102-Methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetic acid

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 312751,4-Dioxane용매

실험 절차

To a solution of 4-(5-methyl-1,3,4-oxadiazol-2-yl)benzaldehyde (5.12 g, 27.2 mmol) in anhydrous MeOH (27 mL) and anhydrous dioxane (27 mL) at −15 to −10° C. (bath temperature) was added several drops of a solution of KOH (7.6 g, 135.4 mmol) in MeOH (27 mL). Bromoform (3 mL, 34.4 mmol) was added, then the remaining KOH/MeOH solution was added over a period of 20 min. The mixture was stirred for 1 hr and the cold bath was removed. After stirring for 30 min, the reaction was put over an ice bath and allowed to warm slowly to room temperature overnight then concentrated to dryness. After dissolving in a minimum amount of H2O, the residue was acidified to pH 1 with 6 M HCl. The aqueous mixture was extracted with EtOAc several times with the addition of brine to the aqueous layer during extraction. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo to give 2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetic acid as a semisolid (6.8 g, quantitative yield). The product was used without further purification.

후처리

  1. customthe cold bath was removed
  2. stirringAfter stirring for 30 min
  3. customthe reaction was put over an ice bath
  4. concentrationthen concentrated to dryness
  5. dissolutionAfter dissolving in a minimum amount of H2O
  6. extractionThe aqueous mixture was extracted with EtOAc several times with the addition of brine to the aqueous layer during extraction
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f135095ea5d14a7f85854b219ad5bc28
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434707B2

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