Sodium ethoxide → 2,3-dihydro-6-fluoro-4-cyano-2-(2-phenylethyl)-4H-1-benzopyran

HRID 487213ノート

反応式

HRID 487213 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][C:7](=O)[C:6]=2[CH:20]=1.C1(C)C(S([CH2:30][N+:31]#[C-])(=O)=O)=CC=CC=1.[O-]CC.[Na+].[Na]>O1CCCC1.C(O)C>[C:30]([CH:7]1[C:6]2[CH:20]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:10][CH:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8]1)#[N:31]

参加物

7

反応物 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 190944442,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-oneHCID 53627694Toluenesulfonylmethyl isocyanide

生成物 1

HCID 190944432,3-dihydro-6-fluoro-4-cyano-2-(2-phenylethyl)-4H-1-benzopyran収率 29.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran-4-one (8.9 gm) was dissolved in anhydrous tetrahydrofuran, and toluenesulfonylmethylisocyanide (12.9 gm) added, followed by freshly prepared sodium ethoxide in ethanol (prepared from sodium (1.5 gm) in ethanol (60 mL) and the mixture stirred at room temperature overnight. The mixture was then concentrated in vacuo, and the residue partitioned between ethyl acetate and H2O, and the organic layer washed with H2O, brine, dried, filtered and evaporated. The residue was purified by column chromatography (2:1 hexanes/diethyl ether) to yield 4-cyano-2,3-dihydro-6-fluoro-2-(2-phenylethyl)-4H-1-benzopyran (2.7 gm, ir: 2250 cm-1).

後処理

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and H2O
  3. washthe organic layer washed with H2O, brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (2:1 hexanes/diethyl ether)

出典と根拠

ORDレコード
ord-f5c5c904d22e4c2a848997a6458a2605
出典データセット
uspto-grants-1994_03
特許番号
US05294635

反応ノート

読み込み中…