Toluene → 7-(3-(Chlorodimethylsilyl)propoxy)-4-methyl-2H-chromen-2-one

HRID 2073589

反応式

HRID 2073589 の反応式
[CH2:1]([O:4][CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].COC1C=C[C:13]2[CH:16]=[CH:17][C:18]([O:20][C:12]=2[CH:11]=1)=[O:19].[CH3:21][SiH:22]([CH3:24])[Cl:23].[C:25]1(C)C=CC=CC=1>>[Cl:23][Si:22]([CH3:24])([CH3:21])[CH2:3][CH2:2][CH2:1][O:4][C:5]1[CH:11]=[C:12]2[C:13]([C:16]([CH3:25])=[CH:17][C:18](=[O:19])[O:20]2)=[CH:7][CH:6]=1

参加物

5

反応物 4

HCID 1140TolueneHCID 10748MethylumbelliferoneHCID 11194Diallyl etherHCID 66108Chlorodimethylsilane2 回

生成物 1

HCID 217155697-(3-(Chlorodimethylsilyl)propoxy)-4-methyl-2H-chromen-2-one

反応条件

温度
110 °C

実験手順

A 1 L 3-necked flask fitted with condenser, thermometer and addition funnel was charged with 87 g (0.4 mol) of the allyl ether of methylumbelliferone formed by Step 1 and 200 ml toluene. While stirring the contents, 15 ml dimethylchlorosilane and 0.5 ml H2PtCl6 were added. With warming of the reaction mixture by an IR lamp, the reaction initiated at 70 degrees C. and quickly rose to 105 degrees C. with reflux. The addition of 40 additional grams of dimethylchlorosilane (0.5 mol total) was adjusted to produce gentle reflux (30 minutes), followed by stirring at 110 degrees C. for 1 hour. The reaction mixture was cooled to room temperature, and the toluene was removed under reduced pressure. The last traces of solvent were removed under high vacuum. The residue (120 g) was dissolved in 1200 ml of acetonitrile for storage and handling. The substitution of DMSO for THF as the solvent in Step 1 eliminated the need for pressure in Step 2 and made the second step generally run cleaner.

後処理

  1. customA 1 L 3-necked flask fitted with condenser
  2. additionthermometer and addition funnel
  3. additionwere added
  4. temperatureWith warming of the reaction mixture by an IR lamp
  5. custominitiated at 70 degrees C
  6. customquickly rose to 105 degrees C
  7. temperaturewith reflux
  8. customto produce gentle
  9. temperaturereflux (30 minutes)
  10. temperatureThe reaction mixture was cooled to room temperature
  11. customthe toluene was removed under reduced pressure
  12. customThe last traces of solvent were removed under high vacuum
  13. dissolutionThe residue (120 g) was dissolved in 1200 ml of acetonitrile for storage and handling

出典と根拠

ORDレコード
ord-47c08a553c754525aee74e65b212226e
出典データセット
uspto-grants-1990_04
特許番号
US04918200

関連ノート

読み込み中…