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

HRID 1585065Notes

Reaction equation

[CH3:1][C:2]1([CH3:12])[CH2:7][O:6][CH:5]([CH2:8][CH2:9][CH:10]=[O:11])[O:4][CH2:3]1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([Mg]Br)=[CH:16][CH:15]=1>C1COCC1>[CH3:1][C:2]1([CH3:12])[CH2:3][O:4][CH:5]([CH2:8][CH2:9][CH:10]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[OH:11])[O:6][CH2:7]1

Participants

Conditions

Temperature: -70 °C

Procedure

To a cold solution of 5,5-dimethyl-1,3-dioxane-2-propanal (2 g, 11.62 mmol) (Step 2) at -70° C. in THF (50 ml), 4-fluorophenyl magnesium bromide (8.7 ml, 2M solution in ether, 17.44 mmol) was added. After stirring at -70° C. for 2 hours, the 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 purified by chromatography to give 3-(5,5-dimethyl-1,3-dioxan-2-yl)-1-(4-fluorophenyl)propan-1-ol (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 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 purified by chromatography

Sources & evidence

ORD record: ord-a182654eaec84518995108bfdb219b63
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05935990

Reaction notes

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