Ethyl 2-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetate → 2-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanol

HRID 344026Notes

Reaction equation

HRID 344026 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][C:14](OCC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 10538520Ethyl 2-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 106083702-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanolYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of ethyl (5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)acetate (1.02 g) and lithium aluminum hydride (0.20 g) in tetrahydrofuran (15 ml was stirred at 0° C. for 2.5 hours. The solution was poured into cold 1N-hydrochlorlc acid, then the resulting mixture was filtered through the celite, and extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate, and evaporated in vacuo to afford 2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanol as a colorless oil (0.85 g).

Workup

  1. additionThe solution was poured into cold 1N-hydrochlorlc acid
  2. filtrationthe resulting mixture was filtered through the celite
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b8716bf5d6c94ce5863f698aa20b58da
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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