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

HRID 78035Notes

Reaction equation

HRID 78035 reaction equation
O1CCCC1.C([O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][O:19]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[CH2:20][CH2:21][CH2:22][CH: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 66707814Ethyl 4-(2-(tetrahydrofuran-2-yl)-ethyl)-benzoic acid ethyl ester

Product 1

HCID 59255503(4-(2-(Tetrahydrofuran-2-yl)-ethyl)-phenyl)-methanolYield 31%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an anhydrous tetrahydrofuran (20 mL) solution of ethyl 4-(2-(tetrahydrofuran-2-yl)-ethyl)-benzoic acid ethyl ester (2.2 g, 9.39 mmol) described in Manufacturing Example 82-1-1 was added diisobutyl aluminum hydride (0.97 M toluene solution, 24.2 mL, 23.5 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere. After stirring for 30 minutes, 15% aqueous potassium sodium tartrate solution (100 mL) was added to the reaction liquid, and stirred for 30 minutes at room temperature. After addition of ethyl acetate (200 mL), 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. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:9 then 2:8) to obtain the title compound (600 mg, 31%).

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
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-489a38f4d44a4b778f97f12294d709d9
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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