Potassium Iodide → (5-Ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methanol

HRID 344045Notes

Reaction equation

HRID 344045 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH:7]2[CH2:12][OH:13].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:19]([O:18][C:16]([CH2:15][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH:7]2[CH2:12][OH:13])=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 54025047(5-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)methanol

Product 1

HCID 53647005(5-Ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of (5-hydroxy-1,2,3,4-tetrahydro-1-naphthyl)methanol (0.20 g), ethyl bromoacetate (0.15 ml), potassium iodide (catalytic amount) and potassium carbonate (0.20 g) in acetonitrile (10 ml) was stirred under reflux for 2.5 hours. The solvent was removed and the residue was partitioned between ether and 1N hydrochloric acid. The organic layer was washed with water and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (n-hexane-ethyl acetate) over silica gel to afford (5-ethoxycarbonylmethoxy-1,2,3,4-tetrahydro-1-naphthyl)methanol (0.29 g) as an oil.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. customThe solvent was removed
  3. customthe residue was partitioned between ether and 1N hydrochloric acid
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed (n-hexane-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-b503d296e2954deabb7df6f8718ab096
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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