Chloroiodomethane → HCID 86709276, compound

HRID 517294Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][NH:11][S:12]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li][CH2:23]CCC.ClCI>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:23])(=[O:14])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1-phenyl-methanesulfonamide (33 g, 100.2 mmol) in tetrahydrofuran (334 mL) at −78° C. was slowly added n-BuLi (2.5 M in hexanes) (100 mL, 250 mmol) via cannula and the reaction was stirred at −78° C. was 2 hours. Chloroiodomethane (8.3 mL, 110 mmol) was then slowly added and the reaction was stirred at −78° C. for one hour, then allowed to warm to room temperature and aged for 16 hours. The reaction was then quenched with saturated NH4Cl and extracted with dichloromethane, dried with MgSO4, concentrated and purified by silica gel column chromatography (0-60% EtOAc in heptane) to give N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1-phenyl-ethenesulfonamide (24 g, 70% yield). LCMS (ESI), m/z, 342. [M+H]+.

Workup

customat −78° C.
stirringthe reaction was stirred at −78° C. for one hour
temperatureto warm to room temperature and aged for 16 hours
customThe reaction was then quenched with saturated NH4Cl
extractionextracted with dichloromethane
dry with materialdried with MgSO4
concentrationconcentrated
custompurified by silica gel column chromatography (0-60% EtOAc in heptane)

Sources & evidence

ORD record: ord-7f2b85da243846f09ee31e0f2cf4656f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115101B2

Reaction notes

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