Sodium hydride → HCID 22252390, compound

HRID 1611992Notes

Reaction equation

HRID 1611992 reaction equation
[H-].[Na+].[CH:3]([Si:6]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[SH:7])([CH3:5])[CH3:4].[H][H].Br[C:17]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:11]([Si:6]([CH:3]([CH3:5])[CH3:4])([CH:8]([CH3:10])[CH3:9])[S:7][C:17]1[CH:18]=[C:19]([O:27][CH3:28])[C:20]([O:25][CH3:26])=[C:21]([O:23][CH3:24])[CH:22]=1)([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 3435097Tris(propan-2-yl)silanethiolHCID 178418361HCID 178418361, compound

Product 1

HCID 22252390HCID 22252390, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.12 g of sodium hydride are added to a solution of 5 g of triisopropylsilanethiol in 100 ml of tetrahydrofuran. When the evolution of hydrogen has ceased, 2.4 g of Pd(PPh3)4, 100 ml of toluene and 6.9 g of 1-bromo-3,4,5-trimethoxybenzene are added, and the reaction mixture is refluxed for 2 hours, and then evaporated in vacuo. Chromatography over silica gel eluted with a mixture of CH2Cl2/heptane (70/30) enables the expected product to be isolated.

Workup

  1. temperaturethe reaction mixture is refluxed for 2 hours
  2. customevaporated in vacuo
  3. washChromatography over silica gel eluted with a mixture of CH2Cl2/heptane (70/30)
  4. customto be isolated

Sources & evidence

ORD record
ord-9464ce1499694ed2bd49aa6ecc06afdd
Source dataset
uspto-grants-2006_01
Patent number
US06992085B2

Reaction notes

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