3-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehyde → (3-(8-(1,3-Dioxolan-2-yl)octyloxy)phenyl)(thiophen-2-yl)methanol

HRID 332653Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[Mg]Br>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[OH:19])[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 3-(8-(1,3-dioxolan-2-yl)octyloxy)benzaldehyde (1.0 g, 3.25 mmol) in THF (30 mL) at −78° C. under an atmosphere of nitrogen, a solution of 2-thienylmagnesium bromide (1M in THF, 4.23 mL, 4.23 mmol) was added over 10 minutes. After stirring at −78° C. for 1 hour, the reaction was allowed to warm to RT and stirred for 16 hours. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-50% ethyl acetate in iso-hexane to afford the title compound (1.12 g, 87%).

Workup

temperatureto warm to RT
stirringstirred for 16 hours
customThe reaction was quenched with saturated aqueous ammonium chloride solution
extractionextracted with ethyl acetate (×3)
washThe combined organic extracts were washed with brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude material was purified by silica gel chromatography
washeluting with 0-50% ethyl acetate in iso-hexane

Sources & evidence

ORD record: ord-ed5b0dca12ec40b5b5c3acb9aca160ab
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877774B2

Reaction notes

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