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

HRID 6523
ノート
印刷プレビュー

反応式

HRID 6523 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 7

HCID 259Bromide ionHCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran4 回HCID 2724682Lithium diisopropylamideHCID 10932944(4S,5S)-2-ethyl-4-methoxymethyl-5-phenyl-2-oxazoline2 回HCID 178418348HCID 178418348、化合物

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d915f9e724c34bff918fbcf5d34e9611
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05248815

反応ノート

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