Triethylamine → 5-(3,3-Dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid ethyl ester

HRID 39291

반응식

HRID 39291 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8](Br)=[CH:9][CH:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:19][C:20]([CH3:24])([CH3:23])[C:21]#[CH:22]>CN(C=O)C.[Cu](I)I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:22]#[C:21][C:20]([CH3:24])([CH3:23])[CH3:19])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 135123,3-Dimethyl-1-butyneHCID 605723Ethyl 5-bromothiophene-2-carboxylate

생성물 1

HCID 581141285-(3,3-Dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid ethyl ester수율 97.3%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 5-Bromo-thiophene-2-carboxylic acid ethyl ester (7 g, 30 mmol), copper iodide (1.2 g, 6 mmol), triethylamine (20 mL) in DMF (100 mL) was degassed in a 350 mL pressure bottle. Then tris(dibenzylideneacetone)dipalladium(0) (2.1 g, 3 mmol) and 3,3-dimethyl-but-1-yne (18.3 mL, 150 mmol) were added and heated at 80 degree for 3 hours. The reaction mixture was filtered on celite and washed with ethyl acetate. The solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined and washed with water. After drying and concentration, the crude residue was purified by flash chromatography to yield 6.9 g (95%) of 5-(3,3-Dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid ethyl ester as a yellow oil.

후처리

  1. customwas degassed in a 350 mL pressure bottle
  2. temperatureheated at 80 degree for 3 hours
  3. filtrationThe reaction mixture was filtered on celite
  4. washwashed with ethyl acetate
  5. additionThe solution was diluted with water
  6. extractionextracted twice with ethyl acetate
  7. washwashed with water
  8. customAfter drying
  9. concentrationconcentration
  10. customthe crude residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-32d5be6c632a4182b5049936e8f684b9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524764B2

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