Sodium → HCID 18687109, compound

HRID 1872568Notes

Reaction equation

HRID 1872568 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[Na]>C(OC(=O)OCC)C>[C:1]([Si:5]([CH3:19])([CH3:20])[O:6][C:7]1[CH:8]=[C:9]([CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[CH:11][CH:12]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 11426411HCID 11426411, compound

Product 1

HCID 18687109HCID 18687109, compoundYield 160.7%

Reagents, catalysts & solvents 1

HCID 7766Diethyl CarbonateSolvent

Procedure

To a solution of ethyl 3-(tertbutyldimethylsilyloxy)phenylacetate (10 g) in 25 ml of diethylcarbonate are added portionwise 0.86 g of sodium and the mixture is refluxed for 2 hours. The solvent is evaporated off and the residue is poured into water (90 ml). The pH is adjusted to pH=6 with acetic acid and the mixture is extracted with diethyl ether. The organic phase is dried over sodium sulfate and cocentrated to dryness to give 10 g of an orange oil which is purified by silica gel chromatography (eluent: petroleum ether/ethyl acetate 95:5), to give 2.45 of the product.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customThe solvent is evaporated off
  3. additionthe residue is poured into water (90 ml)
  4. extractionthe mixture is extracted with diethyl ether
  5. dry with materialThe organic phase is dried over sodium sulfate

Sources & evidence

ORD record
ord-ff9261d604804522ac916701ff9a5495
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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