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

HRID 713982Notes

Reaction equation

HRID 713982 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 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 silica gel column
  8. washeluted with EtOAc in hexanes from 0 to 60%

Sources & evidence

ORD record
ord-2aeaeb20c55d447493a6007b2b23ad51
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

Loading…