Water → HCID 84664309, compound

HRID 1919867Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][CH:14]1[CH2:17][CH2:16][CH2:15]1.CN([CH:21]=[O:22])C.O>C1COCC1>[CH:14]1([S:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:21]=[O:22])[CH2:17][CH2:16][CH2:15]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of n-butyllithium (7.35 mL of a 1.6 M solution in hexanes, 11.7 mmol) in dry THF (15 mL) at −78° C. was added dropwise over 10 minutes a solution of (2-bromophenyl)(cyclobutyl)sulfane (1.19 g, 4.89 mmol) in dry THF (15 mL) and the resulting solution stirred at −78° C. for 30 minutes. Anhydrous DMF (1.14 mL, 14.7 mmol) was then added, and the solution stirred at −78° C. for 5 minutes, before allowing to warm to room temperature and stirring for a further 1 hour. Water was then added, and the volatiles removed in vacuo, before extracting the mixture with ethyl acetate (×3). The combined organics were washed with brine, then dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was purified using flash column chromatography on silica gel (eluting with a gradient of 0 to 5% ethyl acetate) to afford 2-(cyclobutylthio)benzaldehyde (450 mg, 2.34 mmol, 48%).

Workup

stirringthe solution stirred at −78° C. for 5 minutes
temperatureto warm to room temperature
stirringstirring for a further 1 hour
customthe volatiles removed in vacuo
extractionbefore extracting the mixture with ethyl acetate (×3)
washThe combined organics were washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated in vacuo
customThe residue was purified
washeluting with a gradient of 0 to 5% ethyl acetate)

Sources & evidence

ORD record: ord-a4f34d8b153f409a9b4c619f8bbac31e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168673B2

Reaction notes

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