Tetrahydrofuran → [2-(2-Methoxy-phenyl)-cyclohexyl]-methanol

HRID 418907Notes

Reaction equation

HRID 418907 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)(=O)C>[CH3:19][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 666520012-(2-Methoxy-phenyl)-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 66651820[2-(2-Methoxy-phenyl)-cyclohexyl]-methanolYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 2-(2-methoxy-phenyl)-cyclohexanecarboxylic acid ethyl ester (2.34 g, 8.9 mmol), lithium aluminum hydride (1.02 g, 26.7 mmol), and tetrahydrofuran (30.0 mL) at room temperature. Stir at rm temperature under nitrogen for 2 hours then add Rochelle's salt and ethyl acetate. Stir 18 hours then separate layers and wash with brine then dry over anhydrous sodium sulfate. Concentrate to yield the titled compound (1.86 g, 95%). TLC Rf=0.08 in 10% ethyl acetate/hexanes. 1H NMR (CDCl3): 7.2 (m, 2H), 6.9 (m, 2H), 3.8 (s, 3H), 3.5 (m, 1H), 3.4 (m, 1H), 3.3 (m, 1H), 2.3 (m, 1H), 1.8 (m, 2H), 1.5 (m, 6H).

Workup

  1. customat room temperature
  2. stirringStir 18 hours
  3. washseparate layers and wash with brine
  4. dry with materialthen dry over anhydrous sodium sulfate
  5. concentrationConcentrate

Sources & evidence

ORD record
ord-ffe279dac1f3476cb5f835aeee407a92
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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