Water → 1-[4-(Diethoxymethyl)phenyl]-3,3-dimethylbutan-1-ol

HRID 911700Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:20][C:21]([CH3:26])([CH3:25])[CH2:22][CH:23]=[O:24].O>C1COCC1.CCOC(C)=O>[CH2:10]([O:9][CH:8]([O:12][CH2:13][CH3:14])[C:5]1[CH:6]=[CH:7][C:2]([CH:23]([OH:24])[CH2:22][C:21]([CH3:26])([CH3:25])[CH3:20])=[CH:3][CH:4]=1)[CH3:11]

Participants

Conditions

Temperature: -78 °C

Procedure

Dissolve 1-bromo-4-(diethoxymethyl)-benzene (6.1 g, 23.55 mmol) in anhydrous THF (150 mL) and cool the solution to −78° C. Add n-butyllithium (11.3 mL, 28.26 mmol, 2.5M solution in hexane) and stir the mixture for 30 min. Add 3,3-dimethylbutyraldehyde (4.7 mL, 35.33 mmol) and stir the mixture for 1 h. Add water and EtOAc. Warm the solution to room temperature and extract the aqueous layer three times with EtOAc. Dry the combined organic extracts with Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (93:7) to give the desired intermediate as a colorless oil (3.8 g, 58%).

Workup

temperatureWarm the solution to room temperature
extractionextract the aqueous layer three times with EtOAc
dry with materialDry the combined organic extracts with Na2SO4
filtrationfilter
concentrationconcentrate in vacuo
customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (93:7)

Sources & evidence

ORD record: ord-292160e7200d4ec78f107263c1d54712
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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