溴离子(溴化物)标准溶液 → 2-(1-Methyl-4-isobutylphenyl)-4-methoxymethyl-5-phenyl-2-oxazoline

HRID 6523

反应方程式

HRID 6523 反应方程式
[CH2:1]([C:3]1[O:4][C@@H:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:6]([CH2:8][O:9][CH3:10])[N:7]=1)[CH3:2].C([N-][CH:21]([CH3:23])[CH3:22])(C)C.[Li+].[CH:25](NC(C)C)(C)[CH3:26].C[Li].[Br-].[Cl-].[Na+].[CH2:37]1[CH2:41]O[CH2:39][CH2:38]1>>[CH3:2][C:1]1([C:3]2[O:4][CH:5]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:6]([CH2:8][O:9][CH3:10])[N:7]=2)[CH:26]=[CH:25][C:37]([CH2:41][CH:21]([CH3:22])[CH3:23])=[CH:38][CH2:39]1

参与物

8

反应物 7

HCID 259溴离子(溴化物)标准溶液HCID 5234Halite (NaCl)HCID 7912二异丙胺HCID 8028四氢呋喃4 次HCID 2724682二异丙基氨基锂HCID 10932944(4S,5S)-2-ethyl-4-methoxymethyl-5-phenyl-2-oxazoline2 次HCID 178418348HCID 178418348，化合物

产物 1

HCID 197938612-(1-Methyl-4-isobutylphenyl)-4-methoxymethyl-5-phenyl-2-oxazoline收率 90%

实验过程

A solution of the compound II (155 g, 0.71 mol) in THF (1.6 L) under nitrogen is cooled to -75° C. in a dry-ice-acetone bath. A solution of 0.8 mol of lithium diisopropylamide, derived from 98 ml of diisopropylamine and 300 ml of 2,3M butylithium (methyllithium) in 750 ml of dry THF is prepared, and added under continuous stirring in the presence of 4.0 Å molecular sieves to the solution of II in dry THF. Stirring is continued for half an hour at -75° C. and 4isobutylphenyliode (bromide) of the amount of 237.6 g (1.95 mol) in 300 ml THF (dry) is added over a period of time of 10 minutes. The resulting, colorless solution is stirred at this temperature for one hour, then subsequently permitted to reach 20° C. The reaction mixture is poured into 3L of saturated aqueous sodium chloride solution, extracted with several portions of petrolether or ether, dried over Na2SO4 or molecular sieves, (4.0 Å) and distilled in vacuo at 0.1 mm Hg to yield 90% of 2-(1-methyl-4-isobutylphenyl)-4-methoxymethyl-5-phenyl-2-oxazoline, having [α]24 -40.5° (c 10.1 in CHCl3) IR (film) 1671 cm-1, NMR (CDCl3, TMS) δ7.33 (s, 5H), 5.33 (d, J=7HZ, 1H), 4.33-3.93 (9, 1H), 3.80-3.33 (m, 2H) 3.43 (3H), 2.87-2.33 (m, 1H), and 2.00-0.68 (m, 12H).

后处理

  1. customis prepared
  2. additionadded
  3. waitis continued for half an hour at -75° C.
  4. stirringThe resulting, colorless solution is stirred at this temperature for one hour
  5. customto reach 20° C
  6. extractionextracted with several portions of petrolether or ether
  7. dry with materialdried over Na2SO4 or molecular sieves, (4.0 Å)
  8. distillationdistilled in vacuo at 0.1 mm Hg

来源与证据

ORD记录
ord-d915f9e724c34bff918fbcf5d34e9611
来源数据集
uspto-grants-1993_09
专利号
US05248815

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