Dimethyl Sulfoxide → HCID 67410119, compound

HRID 1802071Notes

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-e996fe7094ab459eba1468f3c405b426
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349849B2

Reaction notes

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