Lithium aluminum hydride → 2-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanol

HRID 2404203Notes

Reaction equation

HRID 2404203 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH:17]3[CH2:22][CH2:21][CH:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:19][CH2:18]3)[CH:12]=2)[CH:7]=1)C.[AlH4-].[Li+]>C1COCC1>[C:23]([CH:20]1[CH2:21][CH2:22][CH:17]([O:16][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[CH:7]=[C:6]([CH2:5][CH2:4][OH:3])[CH:15]=[CH:14]3)[CH2:18][CH2:19]1)([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 66926519[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-acetic acid ethyl ester

Product 1

HCID 669266452-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanolYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of [6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-acetic acid ethyl ester (250 mg, 0.68 mmol) in THF (10 mL) was added 1.0 M of lithium tetrahydroaluminate in THF (2 mL, 2 mmol) at 0° C. After stirred at room temperature for 2 hrs, the solution was quenched with ethyl acetate (1 mL), then added Rochelle's salt aqueous (1.5 mL). The solution was stirred for 1 hr, then extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated. The resulting crude was purified via a silica gel column eluted with EtOAc in hexanes from 0 to 60% to give white precipitate (0.17 g, yield: 77%). ESI-MS: 327.20 (M+H)+.

Workup

  1. customthe solution was quenched with ethyl acetate (1 mL)
  2. stirringThe solution was stirred for 1 hr
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude was purified via a silica gel column
  8. washeluted with EtOAc in hexanes from 0 to 60%

Sources & evidence

ORD record
ord-94424ebf76c447e7ae3073ff16b4d814
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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