Ethyl 1-(2,3-dimethoxybenzyl)cycloheptane Carboxylate → [1-(2,3-Dimethoxybenzyl)cycloheptyl]methanol

HRID 54152Notes

Reaction equation

HRID 54152 reaction equation
[CH3:1][O:2][C:3]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][C:6]1([C:13](OCC)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][C:6]1([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 19961186Ethyl 1-(2,3-dimethoxybenzyl)cycloheptane CarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 19961173[1-(2,3-Dimethoxybenzyl)cycloheptyl]methanolYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude ester (26 g, 82 mmol, from Step B above), was dissolved in 400 mL anhydrous THF to which was added solid LiAlH4 (4.6 g, 123 mmol) in small portions at room temperature. The reaction was stirred at room temperature until TLC indicated completion. The reaction was then quenched with 1M HCl and diluted with ether. The layers were separated, and the organic layer was washed with 1M HCl, water, and brine. The organic layer was dried over MgSO4, filtered and evaporated. The resulting oil was purified by silica gel chromatography to give 20 g of the title product as a colorless oil.

Workup

  1. customThe reaction was then quenched with 1M HCl
  2. additiondiluted with ether
  3. customThe layers were separated
  4. washthe organic layer was washed with 1M HCl, water, and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3c4b084256304b19a984492f52d51802
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

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