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Dimethylformamide → HCID 21947595、化合物

HRID 2214431
ノート
印刷プレビュー

反応式

HRID 2214431 の反応式
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH:3]=[CH2:4].B1[CH:21]2[CH2:22]CC[CH:17]1[CH2:18][CH2:19][CH2:20]2.C(=O)([O-])[O-].[K+].[K+].C[N:32](C=O)C>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:22][C:21]1[N:32]=[CH:17][C:18]([CH2:4][CH2:3][CH2:2][CH2:1][N:5]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:15])=[CH:19][CH:20]=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

8

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 339432N-(3-Buten-1-yl)phthalimide2 回

生成物 1

HCID 21947595HCID 21947595、化合物

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
触媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a suspension of 2-3 (12.7 g, 63.2 mmol) was added a solution of 9-BBN in THF (132 mL of a 0.5 M solution, 65.8 mmol). After stirring for 15 hours, potassium carbonate powder (14.5 g, 105 mmol) and 2-3 (12.7 g, 52.7 mmol) was added. To this mixture was then added a premixed, degassed, aged (80° C. for 30 minutes with vigorous stirring) suspension of Pd(OAc)2 (1.78 g, 7.9 mmol) and DPPF (4.96 g, 8.9 mmol) in DMF (50 mL) via a cannula, and the resulting mixture degassed with argon bubbling for 30 minutes. The mixture was then heated at 70° C. for 3 hours. Following cooling, the mixture was reduced to a thick slurry, diluted with ether, washed with water and brine. The organics were dried over MgSO4 and concentrated to give a brown oil. This residue was chromatographed on silica gel (40–60% EtOAc/hexanes) to give 2-4 (9.6 g) as a yellow solid.

後処理

  1. additionTo this mixture was then added a premixed
  2. customdegassed
  3. customthe resulting mixture degassed with argon bubbling for 30 minutes
  4. temperatureFollowing cooling
  5. additiondiluted with ether
  6. washwashed with water and brine
  7. dry with materialThe organics were dried over MgSO4
  8. concentrationconcentrated
  9. customto give a brown oil
  10. customThis residue was chromatographed on silica gel (40–60% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-a3f5605e237b4ca68423c0c568881fbb
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07109191B2

反応ノート

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