Triethylamine → 2-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1 1-dimethylethyl)dimethylsilyl)oxymethyl)-1-O-methanesulfonylcyclobutanol

HRID 5969Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:24])([CH3:23])[O:6][CH2:7][CH2:8][CH:9]1[CH:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][CH:10]1[OH:22])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl>[CH3:4][C:2]([Si:5]([CH3:23])([CH3:24])[O:6][CH2:7][CH2:8][CH:9]1[CH:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][CH:10]1[O:22][S:33]([CH3:32])(=[O:35])=[O:34])([CH3:1])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2-((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethyl-silyl)oxymethyl)cyclobutanol (160 mg, 0.43 mmol) from Step B was dissolved in 2 mL of methylene chloride and the resultant solution was cooled to 0° C. Triethylamine (120μL) was added, followed by 36 μL of methanesulfonyl chloride. After stirring the reaction mixture for 30 min at 0° C., it was concentrated in vacuo and the residue was purified on a silica gel column eluted with 10% ethyl acetate in hexane to give 180 mg (89% yield) of the title compound.; MS DCI-NH3M/Z: 447 (M+H)+, 464 (M+NH4)+.

Workup

concentrationit was concentrated in vacuo
customthe residue was purified on a silica gel column
washeluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record: ord-0e97936974da410d9d6fe7fab4bd1b46
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246931

Reaction notes

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