1-Dodecyne → 5-(Dodec-1-YN-1-YL)-2-hydroxybenzene-1,3-dicarbaldehyde

HRID 736586

反応式

HRID 736586 の反応式
[CH:1]([C:3]1[CH:8]=[C:7](Br)[CH:6]=[C:5]([CH:10]=[O:11])[C:4]=1[OH:12])=[O:2].[CH:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(#N)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]([C:3]1[CH:8]=[C:7]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:6]=[C:5]([CH:10]=[O:11])[C:4]=1[OH:12])=[O:2]

参加物

6

反応物 2

HCID 698211-DodecyneHCID 52602065-Bromo-2-hydroxybenzene-1,3-dicarbaldehyde

生成物 1

HCID 597108655-(Dodec-1-YN-1-YL)-2-hydroxybenzene-1,3-dicarbaldehyde収率 46%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178419050HCID 178419050、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

2,6-Diformyl-4-bromophenol (2.50 g, 10.9 mmol), 1-dodecyne (2.00 g, 12.0 mmol), CuI (65 mg, 0.33 mmol), and bis(triphenylphosphine)palladium)II) dichloride were suspended in degassed acetonitrile (MeCN) (5 mL) and degassed benzene (1 mL). The yellow suspension was sparged with argon for 30 min and degassed Et3N (1 mL) was added. The resulting brown suspension was sealed in a pressure vial, warmed to 80° C. and held there for 12 h. The mixture was then partitioned between EtOAc and KHSO4 solution. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated under reduced pressure. The dark yellow oil was purified by column chromatography on silica gel (25% Et2O in hexanes) to give 1.56 g (46%) of the title compound.

後処理

  1. customdegassed benzene (1 mL)
  2. customThe yellow suspension was sparged with argon for 30 min
  3. customdegassed Et3N (1 mL)
  4. additionwas added
  5. customThe resulting brown suspension was sealed in a pressure vial
  6. customThe mixture was then partitioned between EtOAc and KHSO4 solution
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure
  11. customThe dark yellow oil was purified by column chromatography on silica gel (25% Et2O in hexanes)

出典と根拠

ORDレコード
ord-81fc3fbce02449e0b0669b26f7226ded
出典データセット
uspto-grants-2009_09
特許番号
US07595368B2

関連ノート

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