Dimethylformamide → 6,7-Dichloro-2-formyl-5-hydroxybenzo[b]thiophene

HRID 370983

反応式

HRID 370983 の反応式
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11].C([Li])CCC.CN(C)[CH:20]=[O:21]>O1CCCC1>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[C:8]([CH:20]=[O:21])[S:7][C:6]=2[C:10]=1[Cl:11]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 132899976,7-Dichloro-1-benzothiophene-5-olHCID 178418339Butyllithium

生成物 1

HCID 132900376,7-Dichloro-2-formyl-5-hydroxybenzo[b]thiophene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 8.7 g of 6,7-dichloro-5-hydroxybenzo[b]thiophene in 50 ml of anhydrous tetrahydrofuran is placed in a 250 ml 3-necked flask and cooled to -25°. To the solution under nitrogen, is added dropwise 42 ml of a solution of 2.5M n-butyllithium at a rate such that the temperature did not rise above -10°. After total addition, the mixture is stirred at 0°-5° for 3 hrs. To the mixture is added 14 ml of anhydrous dimethylformamide over a period of 20 mins. The reaction mixture is allowed to warm to room temperature and stirred for 1 hr. Quenching with 400 ml of 2N hydrochloric acid, followed by extraction with ethyl acetate, gives a precipitate. Recrystallization from acetone-hexane affords 6.5 g of 6,7-dichloro-2-formyl-5-hydroxy-benzo[b]thiophene, mp 197°-198°.

後処理

  1. temperaturecooled to -25°
  2. customdid not rise above -10°
  3. additionAfter total addition
  4. stirringstirred for 1 hr
  5. customQuenching with 400 ml of 2N hydrochloric acid
  6. extractionfollowed by extraction with ethyl acetate
  7. customgives a precipitate
  8. customRecrystallization from acetone-hexane

出典と根拠

ORDレコード
ord-89a7fe1f5cec422fb7718e66405f20c6
出典データセット
uspto-grants-1985_07
特許番号
US04528399

関連ノート

読み込み中…