N-Hydroxyphthalimide → (E,E,E)-N-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyloxy)phthalimide

HRID 1066030노트

반응식

HRID 1066030 반응식
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH2:44]([CH2:54][C:55](=[CH:57][CH2:58][CH2:59]/[C:60](=[CH:62]/[CH2:63]O)/[CH3:61])[CH3:56])/[CH:45]=[C:46](/[CH2:48][CH2:49][CH:50]=[C:51]([CH3:53])[CH3:52])\[CH3:47]>C1COCC1>[CH3:61]/[C:60](/[CH2:59][CH2:58]/[CH:57]=[C:55](\[CH3:56])/[CH2:54][CH2:44]/[CH:45]=[C:46](\[CH3:47])/[CH2:48][CH2:49][CH:50]=[C:51]([CH3:53])[CH3:52])=[CH:62]\[CH2:63][O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7]

참가 물질

6

반응물 4

HCID 10665N-HydroxyphthalimideHCID 11776Triphenylphosphine2회HCID 5462977Diethyl azodicarboxylate2회HCID 865915033,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol

생성물 1

HCID 15524010(E,E,E)-N-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyloxy)phthalimide수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of N-hydroxyphthalimide (1.12 g, 6.88 mmol), triphenylphosphine (1.81 g, 6.88 mmol) and diethylazodicarboxylate (1.19 mL, 7.57 mmol) in anhydrous THF (60 mL) was treated with geranylgeraniol (2.0 g, 6.88 mmol) and the resulting mixture was stirred for 18 h at rt. After addition of triphenylphosphine (0.905 g, 3.44 mmol) and diethylazodicarboxylate (0.595 mL, 3.78 mmol), the mixture was stirred at rt for another 24 h. The solvent was evaporated and the residue was purified on 230-400 mesh silica gel (Macherey-Nagel Silica Gel 60 Art. Nr. 81538) eluting with CH2Cl2-hexane (6:4) and collecting 10 mL fractions. The appropriate fractions were combined and evaporated to give the intermediate 20 (2.63 g, 88%) as a white solid: mp 40-41° C.; 1H-NMR (CDCl3, 80 Mhz) δ 1.58 (s, 9H, 3×CH3), 1.67 (s, 3H, CH3), 1.71 (s, 3H, CH3), 2.03 (m, 12H, 6×CH2), 4.71 (d, 2H, J=7.2 Hz, CH2), 5.07 (br, 3H, 3×CH), 5.52 (t, 1H, J=7.2 Hz, CH), 7.73 (m, 4H, Ar); Anal. Calcd for C28H37NO3 (MW 435.3); C, 77.26; H, 8.50; N, 3.22. Found: C, 77.38; H, 8.38; N, 3.04.

후처리

  1. stirringthe mixture was stirred at rt for another 24 h
  2. customThe solvent was evaporated
  3. customthe residue was purified on 230-400 mesh silica gel (Macherey-Nagel Silica Gel 60 Art. Nr. 81538)
  4. washeluting with CH2Cl2-hexane (6:4)
  5. customcollecting 10 mL fractions
  6. customevaporated

출처 및 근거

ORD 기록
ord-928d1de6dc6447b089465f4a55cecdc5
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06242433B1

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