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

HRID 963715Notes

Reaction equation

HRID 963715 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-42027d98086d4119998784f81938ba65
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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