Dimethyl Sulfoxide → HCID 67410119, compound

HRID 709855Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[C:24]([CH:29]([OH:31])[CH3:30])[CH:25]=[N:26]2)=[CH:21][CH:20]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].CCN(CC)CC>C(Cl)Cl.O>[CH2:11]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[C:24]([C:29](=[O:31])[CH3:30])[CH:25]=[N:26]2)=[CH:21][CH:20]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of oxalyl chloride (987 mg, 7.8 mmol, 1.5 eq.) in dry CH2Cl2 (40 mL) was added slowly DMSO (1.6 g, 20.8 mmol, 4 eq.) at −78° C. under N2 After 30 min, 1-(7-(heptyloxy)quinolin-3-yl)ethanol (1.5 g, 5.2 mmol) was added dropwise at −78° C. The mixture was stirred for 2 h at −78° C., and then Et3N (3.2 g, 31 mmol, 6 eq.) was added at −78° C. After 20 min, the mixture was warmed to room temperature. Then the reaction mixture was added water (30 mL), extracted (DCM), washed (brine), dried (Na2SO4), filtered and evaporated to dryness to give the crude product, which was purified by silica gel column chromatography (PE-EA, 10:1) to give 1-(7-(heptyloxy)quinolin-3-yl)ethanone as yellow solid (1.08 g, yield 73%). ESI-MS: 286 (M+H)+.

Workup

waitAfter 20 min
temperaturethe mixture was warmed to room temperature
extractionextracted (DCM)
washwashed (brine)
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated to dryness
customto give the crude product, which
customwas purified by silica gel column chromatography (PE-EA, 10:1)

Sources & evidence

ORD record: ord-2ffa6121252f45739be9d5fb339b25ae
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181191B2

Reaction notes

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