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Dimethylformamide → 6-cyclohexyl-3-formyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 505789
ノート
印刷プレビュー

反応式

HRID 505789 の反応式
[CH:1]1([C:7]2[C:8]3[S:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][C:9]=3[N:10]([CH2:18][O:19][CH3:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li]C(CC)C.CN(CCN(C)C)C.CN([CH:43]=[O:44])C>C1COCC1>[CH:1]1([C:7]2[C:8]3[S:23][C:22]([C:24]([OH:26])=[O:25])=[C:21]([CH:43]=[O:44])[C:9]=3[N:10]([CH2:18][O:19][CH3:20])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 497740056-Cyclohexyl-4-(methoxymethyl)-5-phenyl-thieno[3,2-b]pyrrole-2-carboxylic acidHCID 178418400CID 53628100

生成物 1

HCID 866270596-cyclohexyl-3-formyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

A solution (0.2 M) of 6-cyclohexyl-4-(methoxymethyl)-5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid in THF was added dropwise to a solution (0.6 M) of sec-BuLi (3 eq.) and TMEDA (3 eq.) in THF at −78° C. After 5 min at −78° C., the resulting solution was treated with DMF (10 eq.) then was allowed to warm up at −10° C. The mixture was quenched with water and poured into aqueous HCl (0.1 N) and extracted with AcOEt. The combined organic phase was dried and concentrated to give the title compound (85%) as a solid, that was used as such.

後処理

  1. customThe mixture was quenched with water
  2. additionpoured into aqueous HCl (0.1 N)
  3. extractionextracted with AcOEt
  4. customThe combined organic phase was dried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e5fba91f9e37406fb1ac206db0b3c60b
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07781431B2

反応ノート

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