6-Methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester → (6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

HRID 278459Notes

Reaction equation

HRID 278459 reaction equation
C([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:17][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:4][OH:3])[CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 110965286-Methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 10058404(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanolYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(RS)-6-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (1.39 g, 5.93 mmol) in THF (20 ml) was added dropwise to a suspension of LiAlH4 (473 mg, 12.46 mmol) at 0-10° C. over 15 min. The reaction was stirred for 1 hr at RT, then quenched by the addition of 4N NaOH (15 ml) and water (20 ml). After stirring vigorously for 15 min the mixture was extracted with EtOAc (25 ml), the aqueous phase was further extracted with EtOAc (2×25 ml), the combined organic extracts were washed with satd. NaCl solution (30 ml), dried (Na2SO4) filtered and evaporated to give the crude product as a clear oil. Chromatographic purification over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (1:3) produced (RS)-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-methanol as a colourless oil (989 mg, 5.14 mmol, 86%), MS m/e=192.1 (M−+).

Workup

  1. customquenched by the addition of 4N NaOH (15 ml) and water (20 ml)
  2. stirringAfter stirring vigorously for 15 min the mixture
  3. extractionwas extracted with EtOAc (25 ml)
  4. extractionthe aqueous phase was further extracted with EtOAc (2×25 ml)
  5. washthe combined organic extracts were washed with satd
  6. dry with materialNaCl solution (30 ml), dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude product as a clear oil
  10. customChromatographic purification over SiO2 (Merck 230-400 mesh)
  11. washeluting with EtOAc-nHexane (1:3)

Sources & evidence

ORD record
ord-a914464580b44e6aa4a0093a246cfe97
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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