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

HRID 505789
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HRID 505789 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e5fba91f9e37406fb1ac206db0b3c60b
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07781431B2

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