Tetrahydrofuran → (4-(2-Furan-2-yl-ethyl)-phenyl)-methanol

HRID 78028Notes

Reaction equation

HRID 78028 reaction equation
O1CCCC1.C([O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][C:11]=1CC)C.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)(=O)C>[O:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[CH2:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 66707797Ethyl 4-(2-furan-2-yl-ethyl)-benzoic acid ethyl ester

Product 1

HCID 59255362(4-(2-Furan-2-yl-ethyl)-phenyl)-methanolYield 99.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an anhydrous tetrahydrofuran (10 mL) solution of ethyl 4-(2-furan-2-yl-ethyl)-benzoic acid ethyl ester (706 mg, 2.89 mmol) described in Manufacturing Example 80-1-2 was added diisobutyl aluminum hydride (0.97 M toluene solution, 7.45 mL, 7.23 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere. After 30 minutes of stirring, 15% aqueous potassium sodium tartrate solution (40 mL) was added to the reaction solution, and stirred for 30 minutes at room temperature. Ethyl acetate (100 mL) was added, and the organic layer and water layer were separated. The organic layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure to obtain the title compound (580 mg, 99%).

Workup

  1. stirringstirred for 30 minutes at room temperature
  2. customthe organic layer and water layer were separated
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-52d00b5b40c1421fb7312d5228ced6f7
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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