Cesium carbonate → HCID 68842094, compound

HRID 1889270Notes

Reaction equation

HRID 1889270 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18]([O:20][CH3:21])=[O:19].Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C=O)C>[CH3:21][O:20][C:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[O:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 68842094HCID 68842094, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5.2 g cesium carbonate and 1.6 g methyl 1-hydroxy-2-naphthoate in 10 ml abs. DMF was added 1.9 g (2-bromethoxy)-tert.butyldimethylsilane and the mixture was reacted for 4 h at 60-80° C. The reaction was poured unto ice and extracted with ethyl acetate twice. The combined organic layers were washed with aqueous sat. sodium hydrogen carbonate solution and brine, dried over magnesium sulphate and concentrated in vacuo to yield 2.7 g of 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-naphthalene-2-carboxylic acid methyl ester.

Workup

  1. customthe mixture was reacted for 4 h at 60-80° C
  2. additionThe reaction was poured unto ice
  3. extractionextracted with ethyl acetate twice
  4. washThe combined organic layers were washed with aqueous sat. sodium hydrogen carbonate solution and brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e6cd377e2c04fb3a4cf4dd44f23aa01
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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