Dimethylformamide → 5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)thiophene-3-carbaldehyde

HRID 49345Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4](/[C:7](/[CH2:24][CH3:25])=[CH:8]/[CH2:9][CH2:10][C:11]([CH2:22][CH3:23])([CH2:20][CH3:21])[O:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])[S:5][CH:6]=1.C([Li])CCC.CN(C)[CH:33]=[O:34].[Cl-].[NH4+]>C1COCC1>[CH2:24](/[C:7](/[C:4]1[S:5][CH:6]=[C:2]([CH:33]=[O:34])[CH:3]=1)=[CH:8]\[CH2:9][CH2:10][C:11]([CH2:22][CH3:23])([O:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])[CH2:20][CH3:21])[CH3:25]

Participants

Conditions

Temperature: -78 °C

Procedure

11 g (24.7 mmol) of [(E)-5-(4-bromo-2-thienyl)-1,1-diethylhept-4-enyloxy]triethylsilane are dissolved in 100 mL of anhydrous THF and the mixture is cooled to −78° C. 10.9 mL (27 mmol) of 2.5 M butyllithium are added slowly and the mixture is stirred for 15 minutes. 2.1 mL (27 mmol) of dimethylformamide are then added and the medium is stirred for 30 minutes and then poured into aqueous ammonium chloride solution. After extraction with ethyl acetate and chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate), the product is obtained in the form of a colourless oil (m=4 g; Y=41%).

Workup

stirringthe medium is stirred for 30 minutes
extractionAfter extraction with ethyl acetate and chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate)
customthe product is obtained in the form of a colourless oil (m=4 g; Y=41%)

Sources & evidence

ORD record: ord-6dbcfd73dfe4425bbfccfb8343299adb
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Reaction notes

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