Sodium Hydroxide → (R)-2-[3-(3-Methoxypropoxy)-4-methoxybenzyl]-3-methylbutan-1-OL

HRID 526664Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][C@H:14]([CH:18]([CH3:20])[CH3:19])[C:15](O)=[O:16])=[CH:11][C:10]=1[O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28].[Mn]([O-])(=O)(=O)=O.[K+].[OH-].[Na+]>C1COCC1.C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[CH:22]=[CH:21][C:12]([CH2:13][C@H:14]([CH:18]([CH3:20])[CH3:19])[CH2:15][OH:16])=[CH:11][C:10]=1[O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28]

Participants

Conditions

Temperature: 40 °C

Procedure

A 100-ml flask is charged under inert atmosphere (nitrogen) with 500 mg (13.18 mmol) of lithium aluminium hydride and 15 ml of THF. The suspension is heated to 40° C., and 2.045 g (6.59 mmol) of (R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methyl-butanoic acid dissolved in 5 ml of THF are added. The mixture is maintained at 40° C. and stirred for two hours, monitoring the course of the reaction by TLC (ethyl acetate:mixture of hexanes 7:3; Rf acid=0.5; Rf alcohol=0.6; spot detecting system with potassium permanganate and UV at 254 nm). At the end of reaction the mixture is cooled to room temperature and 0.5 ml of water, 0.5 ml of a 15% w/w solution of NaOH and another 0.5 ml of water are added dropwise. The mixture is diluted with toluene, filtered on Celite and concentrated to constant residue, obtaining 1.90 g (yield 97%) of product in the form of a colourless dense oil.

Workup

additionare added
temperatureThe mixture is maintained at 40° C.
customAt the end of reaction the mixture
temperatureis cooled to room temperature
filtrationfiltered on Celite
concentrationconcentrated to constant residue

Sources & evidence

ORD record: ord-ab75b76ac2a8485fa8e2d4c1e080f2c2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346745B2

Reaction notes

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