Diethyl Ether → [2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-methanol

HRID 418922Notes

Reaction equation

HRID 418922 reaction equation
C([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[O:19][CH3:20])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[CH3:20][O:19][C:12]1[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=1[CH:7]1[CH2:8][CH2:9][CH2:10][CH:6]1[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 666519992-(2,5-Dimethoxy-phenyl)-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 66652073[2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-methanolYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 2-(2,5-dimethoxy-phenyl)-cyclopentanecarboxylic acid ethyl ester (4.5 g, 16 mmol) in tetrahydrofuran (80 ml), add a 1.0M solution of lithium aluminum hydride in tetrahydrofuran (49 ml, 49 mmol), and stir at room temperature for 1 hour. Pour slowly into a mixture of ether and aqueous Rochelle's Salt, stir over night, separate layers, wash organic with brine, dry and concentrate to give the title compound (3.6 g, 94%): 1H NMR (CDCl3) δ 6.82-6.70 (m, 3H), 3.82 (s, 3H), 3.77 (s,−3H), 3.66-3.60 (m, 1H), 3.30-3.23 (m, 1H), 3.07-3.01 (m, 1H), 2.53-2.43 (m, 1H), 2.14-2.11 (m, 1H), 2.03-1.98 (m, 1H), 1.94-1.89 (m, 2H), 1.81-1.71 (m, 2H), 1.43-1.38 (m, 1H).

Workup

  1. stirringstir over night
  2. customseparate layers
  3. washwash organic with brine
  4. customdry
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-bd80c1a7a92246ae85c23f1c950d982a
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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