Tetrahydrofuran → 4,5-Dicyclopropyl-2-ethoxybenzenemethanol

HRID 531054Notes

Reaction equation

HRID 531054 reaction equation
C1COCC1.[CH:6]1([C:9]2[C:18]([CH:19]3[CH2:21][CH2:20]3)=[CH:17][C:12]([C:13](OC)=[O:14])=[C:11]([O:22][CH2:23][CH3:24])[CH:10]=2)[CH2:8][CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH:6]1([C:9]2[C:18]([CH:19]3[CH2:21][CH2:20]3)=[CH:17][C:12]([CH2:13][OH:14])=[C:11]([O:22][CH2:23][CH3:24])[CH:10]=2)[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 90423797Methyl 4,5-dicyclopropyl-2-ethoxybenzoate

Product 1

HCID 904239324,5-Dicyclopropyl-2-ethoxybenzenemethanolYield 97.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A THF (15 mL) solution of methyl 4,5-dicyclopropyl-2-ethoxybenzoate (3.26 g) was added at 0° C. to a mixture of lithium aluminum hydride (1.09 g) and THF (65 mL), and the resultant mixture was stirred at room temperature for 1 hour in a nitrogen atmosphere. Water (1 mL), a 1 M aqueous sodium hydroxide solution (1 mL), and water (3 mL) were added in this order to the reaction mixture at 0° C., and the mixture was filtered through celite. Then, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to obtain the title compound (2.84 g).

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationThen, the filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5ec82e1b01784cc8ab4f28c7b3cf4312
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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