三苯基膦 → (R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione

HRID 1069154笔记

反应方程式

HRID 1069154 反应方程式
[OH:1][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1O.CCOC(/N=N/C(OCC)=O)=O>>[F:35][C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[O:1][CH2:2][C@H:3]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH3:4]

参与物

5

反应物 4

HCID 11776三苯基膦HCID 949522,5-二氟苯酚HCID 641846(R)-(-)-2-酞酰亚胺基-1-丙醇HCID 5462977偶氮二甲酸二乙酯

产物 1

HCID 69472648(R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione收率 63.9%

实验过程

A solution of 15.8 g (77 mmol) of (R)-2-(2-hydroxy-1-methylethyl)-1H-isoindole-1,3(2H)-dione, 24.2 g (92 mmol) of triphenylphosphine and 10.0 g (77 mmol) of 2,5-difluorophenol was stirred while 18.2 mL (116 mmol) of diethylazodicarboxylate was added dropwise. After stirring at ambient temperature overnight, solvent was removed and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil which was chromatographed on silica gel to give 15.6 g of the title compound of Step C as an oil, 1H NMR (CDCl3) δ 1.55 (d, 3H), 4.25 (m, 1H), 4.8 (m, 1H), 6.55 (m, 1H), 6.65 (m, 1H), 6.9 (m, 1H), 7.7 (m, 2H), 7.85 (m, 2H).

后处理

  1. additionwas added dropwise
  2. customsolvent was removed
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate was washed with water and brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgave an oil which
  8. customwas chromatographed on silica gel

来源与证据

ORD记录
ord-b4fb6d163e9c41feb718d9aad647cf38
来源数据集
uspto-grants-2001_06
专利号
US06251947B1

反应笔记

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