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

HRID 2073588

Reaction equation

HRID 2073588 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].[CH3:8][C:9]1[C:15]2C=CC(O)=[CH:19][C:14]=2[O:13][C:11](=[O:12])[CH:10]=1.[CH3:21][SiH:22]([CH3:24])[Cl:23].C1(C)C=CC=CC=1>O1CCCC1>[Cl:23][Si:22]([CH3:24])([CH3:21])[CH2:3][CH2:2][CH2:1][O:4][C:5]1[CH:19]=[C:14]2[C:15]([C:9]([CH3:8])=[CH:10][C:11](=[O:12])[O:13]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11194Diallyl etherHCID 66108ChlorodimethylsilaneHCID 52805674-Methylumbelliferone

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

A glass pressure bottle was charged with 21.6 g of the allyl ether of 4-methylumbelliferone, 11 mls of dimethylmonochlorosilane, 25 mls of toluene and 0.1 cc of a 0.1M H2PtCl6 solution in tetrahydrofuran. The mixture was heated to 140 degrees C. at 40 psi for 15 hours. Toluene was removed by rotary evaporation. The title product was recovered in a yield of 27 g at greater than 70% purity as determined by proton NMR. A broad UV absorption spectrum was observed with maxima at 319.5, 281, 248 and 223 nanometers (nm). The extinction coefficient at 319.5 was greater than 20,000. Fluorescence spectra obtained after excitation at 384 nm gave maxima at 390 (v.s.), 421, 521, and 585 nm.

Workup

  1. customToluene was removed by rotary evaporation
  2. customThe title product was recovered in a yield of 27 g at greater than 70% purity
  3. customA broad UV absorption spectrum
  4. customFluorescence spectra obtained after excitation at 384 nm
  5. customgave maxima at 390 (v.s.), 421, 521, and 585 nm

Sources & evidence

ORD record
ord-60001957ff6e4c93b98e1b100a372a58
Source dataset
uspto-grants-1990_04
Patent number
US04918200

Linked notes

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