Hydrochloric Acid → Trityl ether

HRID 1169854Notes

Reaction equation

[OH2:1].Cl.[C:3](NO)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>O1CCOCC1>[C:3]([O:1][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a flask charged with THI (21.20 mmol, 4.88 g) was added water (25 ml) and 1N aqueous HCl (21.2 ml, 21.2 mmol). After all solids dissolved, a solution of trityl hydroxylamine (25.44 mmol, 7.00 g) in dioxane (55 ml) was added and the reaction was maintained at 50° C. for 4 h. At completion, the reaction was cooled room temperature and the solution was adjusted to pH=7 by addition of 1N aqueous NaOH. The neutralized solution was then concentrated to a plastic mass, which was purified by flash chromatography on silica gel [10% MeOH/1% NH4OH (5% wt. solution in water) in DCM] to provide the trityl-ether as clear plastic. Treatment of the plastic mass with hexane and concentration provided a white foam, which could be dried under vacuum to a flaky solid (10.00 g, 97% yield).

Workup

additionTo a flask charged with THI (21.20 mmol, 4.88 g)
dissolutionAfter all solids dissolved
temperatureAt completion, the reaction was cooled room temperature
concentrationThe neutralized solution was then concentrated to a plastic mass, which
customwas purified by flash chromatography on silica gel [10% MeOH/1% NH4OH (5% wt. solution in water) in DCM]

Sources & evidence

ORD record: ord-ee135757984e4729af0952ac4201e990
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825150B2

Reaction notes

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