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

HRID 2359166

反応式

HRID 2359166 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7a07df32fa594603b3e59ed3b4c16b04
出典データセット
uspto-grants-2014_04
特許番号
US08685975B2

関連ノート

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