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

Carbon Dioxide → 2,5-Bis[(tetrahydropyran-2-yl)oxymethyl]benzoic acid

HRID 1766853
ノート
印刷プレビュー

反応式

HRID 1766853 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH:10]=[CH:9][C:8]=1[CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1.[C:29](=[O:31])=[O:30].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]1[O:22][CH2:21][C:8]1[CH:9]=[CH:10][C:11]([CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:12][C:7]=1[C:29]([OH:31])=[O:30]
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

8

反応物 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 211104512-Bromo-1,4-bis[(tetrahydropyran-2-yl)oxymethyl]benzeneHCID 178418339Butyllithium

生成物 1

HCID 211104372,5-Bis[(tetrahydropyran-2-yl)oxymethyl]benzoic acid収率 50%

試薬・触媒・溶媒 3

HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

n-Butyllithium (1.57 M hexane solution; 8.33 ml, 13.1 mmol) was added dropwise to a solution of 2-bromo-1,4-bis[(tetrahydropyran-2-yl)oxymethyl]benzene (3.55 g, 9.22 mmol) obtained from Example 1-(2) in tetrahydrofuran (30 ml) with stirring at −78° C. After the mixture was stirred at the same temperature for 20 minutes, carbon dioxide gas was introduced thereto for 40 minutes. The resulting mixture was stirred at the same temperature for 1 hour, and then the reaction was stopped by addition of a saturated aqueous solution of ammonium chloride. The mixture was warmed to 0° C., and then the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to afford the residue. The residue was subjected to chromatography on a silica gel (100 g) column (eluent; ethyl acetate:hexane=1:3) to give the title compound (1.63 g, 50% yield) as a colorless oil.

後処理

  1. stirringAfter the mixture was stirred at the same temperature for 20 minutes
  2. stirringThe resulting mixture was stirred at the same temperature for 1 hour
  3. temperatureThe mixture was warmed to 0° C.
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto afford the residue

出典と根拠

ORDレコード
ord-cbea3d04070e40bda3839db7f1e42926
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07230023B2

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