Bromide ion → 2-(1-Methyl-4-isobutylphenyl)-4-methoxymethyl-5-phenyl-2-oxazoline

HRID 6523

반응식

HRID 6523 반응식
[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

참가 물질

8

반응물 7

HCID 259Bromide ionHCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran4회HCID 2724682Lithium diisopropylamideHCID 10932944(4S,5S)-2-ethyl-4-methoxymethyl-5-phenyl-2-oxazoline2회HCID 178418348HCID 178418348, 화합물

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d915f9e724c34bff918fbcf5d34e9611
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248815

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