Hydrochloric Acid → 1-Benzothiophene-2-carbaldehyde

HRID 542767Notes

Reaction equation

C([Li])CCC.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7]1.CN(C)[CH:17]=[O:18].Cl>CCCCCC.C(OCC)C>[S:6]1[C:7]([CH:17]=[O:18])=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 31.25 ml of a 1.6M solution of n-butyl lithium in hexane and 100 ml of dry diethyl ether at -20° C. was added a solution of 6.7 g of 1-benzothiophene in 100 ml of dry diethyl ether. The mixture was stirred at -20° C. for 2 hours. A solution of 3.8 ml of dimethylformamide and 10 ml of dry diethyl ether was added and the reaction was allowed to warm to 0° C. The reaction was stirred an additional 1 hour at 0° C., at which time 75 ml of 1N hydrochloric acid were added. After stirring for 15 minutes, the layers were separated and the aqueous layer was extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate and evaporated to dryness. The resulting oil was stored at about 0° C. for 3 days, at which time a solid formed. The solid weighed 8.5 g and was identified as the desired subtitled intermediate based upon the mass spectral and proton NMR data.

Workup

temperatureto warm to 0° C
additionwere added
stirringAfter stirring for 15 minutes
customthe layers were separated
extractionthe aqueous layer was extracted with diethyl ether
dry with materialThe combined organic extracts were dried over magnesium sulfate
customevaporated to dryness
waitThe resulting oil was stored at about 0° C. for 3 days, at which time
customa solid formed

Sources & evidence

ORD record: ord-293a4aa75df44572b53f23f8156765e3
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659717

Reaction notes

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