Tetrahydrofuran → (4,5-Dicyclopropyl-2-isopropoxyphenyl)methanol

HRID 531028Notes

Reaction equation

HRID 531028 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][CH:23]([CH3:25])[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][CH:23]([CH3:25])[CH3:24])[CH:10]=2)[CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 90423073Methyl 4,5-dicyclopropyl-2-isopropoxybenzoate

Product 1

HCID 90423712(4,5-Dicyclopropyl-2-isopropoxyphenyl)methanolYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A THF (15 mL) solution of methyl 4,5-dicyclopropyl-2-isopropoxybenzoate (5.90 g) was added at 0° C. to a mixture of lithium aluminum hydride (1.71 g) and THF (85 mL), and the resultant mixture was stirred at room temperature for 30 minutes in a nitrogen atmosphere. Water (1.8 mL), a 1 M aqueous sodium hydroxide solution (1.8 mL), and water (5.4 mL) were added in this order to the reaction mixture at 0° C. The mixture was filtered through celite, and 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 (5.22 g).

Workup

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

Sources & evidence

ORD record
ord-1f8a24536d034be085b64ff81b699c16
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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