5,5-Dimethyl-1,3-dioxane-2-propionaldehyde → 3-(5,5-Dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-ol

HRID 29045Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:21])[CH2:16][O:15][CH:14]([CH2:17][CH2:18][CH:19]=[O:20])[O:13][CH2:12]1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:19]([OH:20])[CH2:18][CH2:17][CH:14]2[O:15][CH2:16][C:11]([CH3:10])([CH3:21])[CH2:12][O:13]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -70 °C

Procedure

4-Fluorophenyl magnesium bromide (8.7 ml, 2M solution in ether, 17.44 mmol) was added to a solution of 5,5-dimethyl-1,3-dioxane-2-propanal (2 g, 11.62 mmol) (Step 2) in THF (50 ml) at −70° C. After stirring at −70° C. for 2 hr, the reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic fractions were combined and washed successively with water and brine. After drying (MgSO4), filtration and concentration, the crude compound (3.5 g) was chromatographed to give α-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-propanol (2.73 g) as a white solid: mp (DSC) 84° C. Anal Calc'd. for C15H21FO3: C, 67.14; H, 7.89. Found: C, 67.18; H, 7.98.

Workup

temperaturethe reaction mixture was warmed to room temperature
stirringstirred overnight
customThe reaction was quenched with water
extractionextracted with ethyl acetate
washwashed successively with water and brine
customAfter drying
filtration(MgSO4), filtration and concentration
customthe crude compound (3.5 g) was chromatographed

Sources & evidence

ORD record: ord-c245a4b0bff340d4893cba7486dbe63c
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420061B2

Reaction notes

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