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

p-Toluenesulphonyl cyanide → (R)-6,8-difluoro-3-[5-((R)-6-fluoro-3-pentylchroman-7-yl)-1,3-dioxan-2-yl]chroman-7-carbonitrile

HRID 2420645
ノート
印刷プレビュー

反応式

HRID 2420645 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[O:8][CH2:7][C@H:6]([CH:13]1[O:18][CH2:17][CH:16]([C:19]3[CH:28]=[C:27]4[C:22]([CH2:23][C@@H:24]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:25][O:26]4)=[CH:21][C:20]=3[F:34])[CH2:15][O:14]1)[CH2:5]2.C([Li])(CC)C.C1(C)C=CC(S([C:49]#[N:50])(=O)=O)=CC=1>C1COCC1.C1CCCCC1.CCOCC>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[C:11]=1[C:49]#[N:50])[O:8][CH2:7][C@H:6]([CH:13]1[O:18][CH2:17][CH:16]([C:19]3[CH:28]=[C:27]4[C:22]([CH2:23][C@@H:24]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:25][O:26]4)=[CH:21][C:20]=3[F:34])[CH2:15][O:14]1)[CH2:5]2
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 3

HCID 87946p-Toluenesulphonyl cyanideHCID 59288368(R)-6,8-difluoro-3-[5-((R)-6-fluoro-3-pentylchroman-7-yl)-1,3-dioxan-2-yl]chromanHCID 178418400CID 53628100

生成物 1

HCID 59288340(R)-6,8-difluoro-3-[5-((R)-6-fluoro-3-pentylchroman-7-yl)-1,3-dioxan-2-yl]chroman-7-carbonitrile

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 8078Cyclohexane溶媒

反応条件

温度
-25 °C

実験手順

800 mg (1.68 mmol) of (R)-6,8-difluoro-3-[5-((R)-6-fluoro-3-pentylchroman-7-yl)-1,3-dioxan-2-yl]chroman are dissolved in 30 ml of THF, and 1.7 ml (2.38 mmol) of a 1.4 M solution of s-butyllithium in cyclohexane are added at −50° C. The batch is warmed at −25° C. for 5 min, left to stir at −70° C. for 2 h, and a solution of 400 mg (2.21 mmol) of p-toluenesulfonyl cyanide in 10 ml of THF is subsequently added at such a rate that the temperature does not exceed −65° C. After 1 h, the batch is allowed to thaw, diluted with ether and washed with dil. hydrochloric acid. The org. phase is dried over sodium sulfate and evaporated, and the crude product is chromatographed on silica gel with toluene, giving (R)-6,8-difluoro-3-[5-((R)-6-fluoro-3-pentylchroman-7-yl)-1,3-dioxan-2-yl]chroman-7-carbonitrile as colourless crystals of m.p. 111° C.

後処理

  1. waitleft
  2. customdoes not exceed −65° C
  3. waitAfter 1 h
  4. washwashed with dil. hydrochloric acid
  5. dry with materialphase is dried over sodium sulfate
  6. customevaporated
  7. customthe crude product is chromatographed on silica gel with toluene

出典と根拠

ORDレコード
ord-b01dbb3303a74031b51a268f8fc25933
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07955664B2

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