Phthalimide → HCID 69332185、化合物

反応式

[CH2:1]([O:8][CH2:9][C@H:10](O)[CH2:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:35]1(=[O:45])[NH:39][C:38](=[O:40])[C:37]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[CH2:1]([O:8][CH2:9][C@@H:10]([N:39]1[C:38](=[O:40])[C:37]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]2[C:35]1=[O:45])[CH2:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

反応物 4

HCID 6809Phthalimide

HCID 11776Triphenylphosphine

HCID 75555Diisopropyl diazene-1,2-dicarboxylate

HCID 14752582HCID 14752582、化合物

生成物 1

HCID 69332185HCID 69332185、化合物収率 83.8%

実験手順

To a stirred solution of 1-benzyloxy-2-(R)-hydroxy-5-hexene (2.18 g, 10.5 mmol), triphenylphosphine (3.32 g, 12.7 mmol) and phthalimide (1.86 g, 12.7 mmol) was added diisopropyl azodicarboxylate (2.62 ml, 12.7 mmol) at rt, and the resulting mixture was stirred for overnight at rt. The mixture was concentrated in vacuo and extracted with EtOAc. The organic layer was washed with water, drying over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent to give 1-benzyloxy-2-(S)-phthalimido-5-hexene (2.95 g, 83%) as a colorless oil: 1H-NMR (CDCl3) δ1.76-1.84 (m, 2 H), 2.06 (dd, J 14.4, 6.8 Hz), 2 H, 2.12-2.22 (m, 1 H), 3.69 (dd, J=10.0, 5.6 Hz, 1 H), 4.00 (t, J=9.6 Hz, 1 H), 4.46 (d, J=12.0 Hz, 1 H), 4.53 (d, J=12.0 Hz, 1 H), 4.51-4.58 (m, 1H), 4.91-4.99 (series of m, 2 H), 5.72-5.79 (m, 1 H)7.21-7.26 (m, 5 H), 7.71-7.83 (series of m, 2 H); MS (ESI) m/z, 336 (M++MH).