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Potassium Carbonate → 2-prop-2-enyl-4H-thieno[2,3-c]furan-6-one

HRID 2173202
ノート
印刷プレビュー

反応式

HRID 2173202 の反応式
Br[C:2]1[S:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[CH3:11][C:12]1(C)[C:16](C)(C)OB(CC=C)O1.C(=O)([O-])[O-].[K+].[K+]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].CN(C=O)C>[CH2:16]([C:2]1[S:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1)[CH:12]=[CH2:11]
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 3

HCID 11430Potassium CarbonateHCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolaneHCID 675165042-bromothieno[2,3-c]furan-6(4H)-one

生成物 1

HCID 690875172-prop-2-enyl-4H-thieno[2,3-c]furan-6-one

試薬・触媒・溶媒 2

HCID 15220664Palladium--triphenylphosphane (1/1)触媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
100 °C

実験手順

In a 15 mL microwave reaction vial was added 2-bromothieno[2,3-c]furan-6(4H)-one (45 mg, 0.205 mmol), 4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane (34.5 mg, 0.205 mmol, 1.0 eq), potassium carbonate (56.8 mg, 0.411 mmol, 2.0 eq) and palladium triphenylphosphane (1:4) (23.7 mg, 0.021 mmol, 0.1 eq). To above mixture was added DMF (1.0 mL), de-gas and filled with N2. The vial was heated to 100° C. for 60 min, cooled down, diluted with EtOAc, washed with aqueous sodium bicarbonate, brine and water. The organic phase was dried over anhydrous Na2SO4, filtered, concentrated. The crude product was purified by flash column chromatography. LC-MS (IE, m/z): 181.2 [M+1]+.

後処理

  1. customIn a 15 mL microwave reaction
  2. customde-gas
  3. additionfilled with N2
  4. temperaturecooled down
  5. additiondiluted with EtOAc
  6. washwashed with aqueous sodium bicarbonate, brine and water
  7. dry with materialThe organic phase was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash column chromatography

出典と根拠

ORDレコード
ord-1af1281819134703a6b23b055dda2752
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056859B2

反応ノート

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