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

HRID 2073589

반응식

HRID 2073589 반응식
[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

참가 물질

5

반응물 4

HCID 1140TolueneHCID 10748MethylumbelliferoneHCID 11194Diallyl etherHCID 66108Chlorodimethylsilane2회

생성물 1

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

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47c08a553c754525aee74e65b212226e
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04918200

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