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

HRID 229716

反応式

HRID 229716 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.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

5

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 2

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), Cul (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, dried MgSO4) and
  9. concentrationconcentrated under reduced pressure
  10. 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-2fe543425c5d41608322a71ab1ccb910
出典データセット
uspto-grants-2009_07
特許番号
US07563890B2

関連ノート

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