ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Diisopropylamine → Methyl 2-acetyl-7-benzyloxy-8-n-propylchroman-2-carboxylate

HRID 1285263
ノート
印刷プレビュー

反応式

HRID 1285263 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:20][C:21]1[C:30]([CH2:31][CH2:32][CH3:33])=[C:29]2[C:24]([CH2:25][CH2:26][CH:27]([C:34]([O:36][CH3:37])=[O:35])[O:28]2)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:38](C1NC=CN=1)(=[O:40])[CH3:39].S([O-])(O)(=O)=O.[K+]>O1CCCC1>[C:38]([C:27]1([C:34]([O:36][CH3:37])=[O:35])[CH2:26][CH2:25][C:24]2[C:29](=[C:30]([CH2:31][CH2:32][CH3:33])[C:21]([O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:22][CH:23]=2)[O:28]1)(=[O:40])[CH3:39]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 7912DiisopropylamineHCID 516920Potassium bisulfateHCID 5389722-AcetylimidazoleHCID 14882998Methyl 7-benzyloxy-8-n-propylchroman-2-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 20250461Methyl 2-acetyl-7-benzyloxy-8-n-propylchroman-2-carboxylate収率 63.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-20 °C

実験手順

A 100 ml 3 neck roundbottom flask was fitted with a magnetic stirring bar, dropping funnel, serum cap, and gas inlet tube, flushed with argon and flame dried. 1.11 g or 1.54 ml (11 mmole) of diisopropylamine and 30 ml dry tetrahydrofuran were added. After cooling to -20° C., 6.43 ml of 1.71M n-butyl lithium (11 mmole) was added dropwise via syringe. The solution was stirred 15 minutes at -10° C. and then cooled to -70° C. 3.40 g (10 mmole) of the product of Example 22 in 20 ml tetrahydrofuran at -70° C. was added dropwise over a period of half hour. After stirring one additional hour at -70° C., 1.27 g (11.5 mmole) of acetylimidazole in 10 ml tetrahydrofuran was added and the reaction mixture allowed to warm slowly to -10° C. 0.5M potassium hydrogen sulfate solution was added until the pH reached 2.0, the layers were separated and 100 ml ethyl acetate was added. The organic layer was washed with 0.5M potassium hydrogen carbonate, twice with water and then dried with anhydrous magnesium sulfate. After filtration, the ethyl acetate was removed by rotary evaporation and the residual oil purified by high pressure liquid chromatography (10% ethyl acetate-hexane) to give 2.42 g (63%) of the title compound as an oil. Calc: C, 72.22; H, 6.85; Found: C, 72.43; H, 6.86.

後処理

  1. customserum cap
  2. customgas inlet tube, flushed with argon
  3. temperatureflame
  4. customdried
  5. temperaturecooled to -70° C
  6. stirringAfter stirring one additional hour at -70° C.
  7. temperatureto warm slowly to -10° C
  8. customthe layers were separated
  9. addition100 ml ethyl acetate was added
  10. washThe organic layer was washed with 0.5M potassium hydrogen carbonate, twice with water
  11. dry with materialdried with anhydrous magnesium sulfate
  12. filtrationAfter filtration
  13. customthe ethyl acetate was removed by rotary evaporation
  14. customthe residual oil purified by high pressure liquid chromatography (10% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-fbc3d81d9bfc498aa6fbd33702195f7f
出典データセット
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04565882

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート