Chloroform → 2-(1-Bromocyclohexyl)-8-cyanomethyl-4-oxo-4H-[1]-benzopyran

HRID 1200186ノート

反応式

HRID 1200186 の反応式
[C-:1]#[N:2].[Na+].C(Cl)(Cl)Cl.[Br:8][C:9]1([C:15]2[O:16][C:17]3[C:25]([CH2:26]Br)=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=[O:21])[CH:20]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[Br:8][C:9]1([C:15]2[O:16][C:17]3[C:25]([CH2:26][C:1]#[N:2])=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=[O:21])[CH:20]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

6

反応物 3

HCID 6212ChloroformHCID 8929Sodium CyanideHCID 146504392-(1-Bromocyclohexyl)-8-bromomethyl-4-oxo-4H-[1]-benzopyran

生成物 1

HCID 146504442-(1-Bromocyclohexyl)-8-cyanomethyl-4-oxo-4H-[1]-benzopyran収率 72.2%

試薬・触媒・溶媒 2

HCID 5963Benzyltrimethylammonium chloride触媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

NaCN (3.88 g, 0.075 mole) was dissolved in water (11 ml) and to the solution was added benzyltrimethylammonium chloride (13.9 g, 0.075 mole). After stirring at 50° C. for 15 minutes, chloroform (120 ml) was added and further 2 -(1-bromocyclohexyl)-8-bromomethyl-4-oxo-4H-[1]-benzopyran (12 g, 0.03 mole) was added. The mixture was stirred for 4 hours. The chloroform layer was washed with water, dried (MgSO4) and then concentrated under reduced pressure to obtain crystals. The crude crystals were recrystallized from ethyl acetate to obtain the title compound (7.5 g) as prisms, m.p. 143°-144° C., yield 72.2%. IR and NMR spectra of this compound were identical with those of the compound obtained in Reference Example 20.

後処理

  1. stirringThe mixture was stirred for 4 hours
  2. washThe chloroform layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto obtain crystals
  6. customThe crude crystals were recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-df6218633a364984a6efef2022b93e8d
出典データセット
uspto-grants-1990_02
特許番号
US04904690

反応ノート

読み込み中…