Water → HCID 22622886、化合物

HRID 840380ノート

反応式

HRID 840380 の反応式
[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([C:13](OC)=[O:14])[CH:11]=[CH:12][C:4]=2[O:3]1.CC(C[AlH]CC(C)C)C.C(O)(C)C.O>O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([CH2:13][OH:14])[CH:11]=[CH:12][C:4]=2[O:3]1

参加物

7

反応物 4

HCID 962WaterHCID 3776IsopropanolHCID 14487Diisobutylaluminum hydrideHCID 10656590methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

生成物 1

HCID 22622886HCID 22622886、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-15 °C

実験手順

10.3 g (46.6 mmol) of (±)-2-methyl-3-oxo-6-(methoxycarbonyl)-3,4-dihydro-2H-1,4-benzoxazine is dissolved in 164 ml of tetrahydrofuran. After 330 ml of toluene is added, the solution is cooled to −15° C. At this temperature, 144.2 ml of a 20% DIBAH solution in toluene is added in drops within 30 minutes. A color change from yellow to orange takes place. After 45 minutes of stirring at −15° C., 31 ml of isopropanol is added in drops at this temperature, and 68 ml of water is added in drops at 0° C. After 2½ hours of vigorous stirring at room temperature, the precipitate that is produced is suctioned off, washed with tetrahydrofuran, and the filtrate is spun in. The residue is chromatographed on silica gel (mobile solvent: methylene chloride/ethanol).

後処理

  1. additionis added in drops at 0° C
  2. stirringAfter 2½ hours of vigorous stirring at room temperature
  3. customthe precipitate that is produced
  4. washwashed with tetrahydrofuran
  5. customThe residue is chromatographed on silica gel (mobile solvent: methylene chloride/ethanol)

出典と根拠

ORDレコード
ord-9e5a0793d9b143029418ccd7890425c4
出典データセット
uspto-grants-2002_04
特許番号
US06365736B1

反応ノート

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