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

HRID 229716

반응식

HRID 229716 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178419050HCID 178419050, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2fe543425c5d41608322a71ab1ccb910
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563890B2

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