Hydrochloric Acid → HCID 10754102, compound

HRID 1527711Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[CH2:15][OH:16].[Li]CCCC.[CH3:22][S:23]SC.Cl>C1COCC1.O>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([S:23][CH3:22])[C:4]=1[CH2:15][OH:16]

Participants

Conditions

Temperature: 0 °C

Procedure

Following the procedure of Flader et al.,22 alcohol 26 (0.521 g, 2.39 mmol) was dissolved in THF (9.0 ml) in a flame-dried 25 mL round bottom flask under Argon, and then cooled to 0° C. At 0° C. nBuLi (2.5 M in hexanes, 2.4 ml, 6.0 mmol) was added slowly, then the ice bath was removed and the reaction was stirred at room temperature for 1 hour. Dimethyldisulfide (0.50 mL, 5.6 mmol) was added slowly at room temperature and the reaction was stirred for another 30 minutes at room temperature before being poured into water, acidified with 2 M HCl, and extracted with ethyl acetate. The organic fractions were combined and washed with brine, dried over MgSO4, and filtered. The resulting solid was purified via flash column chromatography (1:4 EtOAc:hexanes) to afford 56 (0.446 g, 1.69 mmol, 71%) as a green solid.

Workup

customthe ice bath was removed
stirringthe reaction was stirred for another 30 minutes at room temperature
extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
customThe resulting solid was purified via flash column chromatography (1:4 EtOAc:hexanes)

Sources & evidence

ORD record: ord-91ca28c617c046af8d45456dfdefea6a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09089605B2

Reaction notes

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