Cesium carbonate → 2-(4-Hydroxy-naphthalen-2-yloxy)-2-methyl-propionic acid ethyl ester

HRID 1727013Notes

Reaction equation

HRID 1727013 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH3:27])([O:7][C:8]1[CH:17]=[C:16]([O:18]COCC[Si](C)(C)C)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[CH3:6])[CH3:2].C[Si](C)(C)CCOCOC1C2C(=CC=CC=2)C=C(O)C=1.BrC(C)(C)C(OCC)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.CCO>CCO>[CH2:1]([O:3][C:4](=[O:28])[C:5]([O:7][C:8]1[CH:17]=[C:16]([OH:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)([CH3:27])[CH3:6])[CH3:2]

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 21887872Ethanol hydrochlorideHCID 690373392-Methyl-2-[4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yloxy]-propionic acid ethyl esterHCID 690383454-(2-Trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ol

Product 1

HCID 690383792-(4-Hydroxy-naphthalen-2-yloxy)-2-methyl-propionic acid ethyl esterYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.58 g (3.90 mmol) of 2-methyl-2-[4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yloxy]-propionic acid ethyl ester (prepared from 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ol, ethyl bromoisobutyrate, cesium carbonate, in analogy to the procedure described in example 14B] was dissolved in 20 ml of EtOH; then, 1.95 ml of HCl/EtOH-solution (6 molar) was added drop by drop. After 7 hours stirring at room temperature, the solvent was removed by evaporation and the residue was partitioned between water and MeCl2. The organic phase was separated, washed with water, dried (MgSO4) and evaporated. The crude product was purified by chromatography over silica gel with a gradient of AcOEt/heptane to give 1.06 g of pure 2-(4-hydroxy-naphthalen-2-yloxy)-2-methyl-propionic acid ethyl ester as light brown oil.

Workup

  1. customthe solvent was removed by evaporation
  2. customthe residue was partitioned between water and MeCl2
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was purified by chromatography over silica gel with a gradient of AcOEt/heptane

Sources & evidence

ORD record
ord-03840e410ddc48febfccfc35bb8331ff
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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