Chlorodimethylsilane → 7-{2-[Chloro(dimethyl)silyl]propoxy}-4-methyl-2H-1-benzopyran-2-one

HRID 1030839Notes

Reaction equation

HRID 1030839 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:16])=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[SiH:17]([Cl:20])([CH3:19])[CH3:18]>C1(C)C=CC=CC=1.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[Cl:20][Si:17]([CH3:19])([CH3:18])[CH:2]([CH3:3])[CH2:1][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:16])=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 66108ChlorodimethylsilaneHCID 2389527-(Allyloxy)-4-methyl-2H-chromen-2-one

Product 1

HCID 198210617-{2-[Chloro(dimethyl)silyl]propoxy}-4-methyl-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 2

HCID 61859Chloroplatinic acidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2.16 g of 7-allyloxy-4-methylcoumarin and 5×10-6 mols chloroplatinic acid hydrosilylation catalyst in 20 ml toluene was slowly added 2.0 g of Me2SiHCl and the mixture was heated at 40°-42° for 6 hrs. Toluene and unreacted silane were then removed at reduced pressure to yield 7{2-(chlorodimethylsilyl)propoxy}-4-methylcoumarin. The 1H-NMR spectrum (ppm) contained signals at 0.2(s) for SiCH3, (6H); 2.4(s) for CH3,(3H); 4.0(t) for CH2O, (2H) and no signal for the allyl moiety.

Workup

  1. temperaturethe mixture was heated at 40°-42° for 6 hrs
  2. customToluene and unreacted silane were then removed at reduced pressure

Sources & evidence

ORD record
ord-38e12346233a4e4599a3ce6c0408381d
Source dataset
uspto-grants-1992_04
Patent number
US05107008

Reaction notes

Loading…