Water → HCID 15290496, compound

HRID 2210783Notes

Reaction equation

HRID 2210783 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:13])[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].O.Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(#N)C>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][O:13][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][CH2:12][CH:3]([CH2:2][OH:1])[CH2:4]2)[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13127828HCID 13127828, compound

Product 1

HCID 15290496HCID 15290496, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 2-hydroxymethyl-5-hydroxy-1,2,3,4-tetrahydronaphthalene (2.72 g,) and potassium carbonate (3.17 g) in acetonitrile, ethyl bromoacetate (2 ml) was added at room temperature. After stirring overnight at room temperature, the reaction mixture was poured into water and extracted with ether. The extract was washed with saturated brine, dried over magnesium sulfate and evaporated. The residue was purified by silica gel chromatography (hexane:ethyl acetate=6:4) to give the title compound (4.10 g) having the following physical data.

Workup

  1. additionwas added at room temperature
  2. extractionextracted with ether
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-d618df0c152644539dd5792db105685f
Source dataset
uspto-grants-1995_10
Patent number
US05461045

Reaction notes

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