Lithium iodide → [2R,3R]-2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanone

HRID 5950

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][CH2:7][C@H:8]1[C@H:12]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C:9]21[O:11][CH2:10]2)([CH3:4])[CH3:3].[I-].[Li+]>C(Cl)Cl>[CH3:4][C:2]([Si:5]([CH3:22])([CH3:23])[O:6][CH2:7][C@H:8]1[C@H:12]([CH2:13][O:14][Si:15]([C:18]([CH3:20])([CH3:19])[CH3:21])([CH3:16])[CH3:17])[CH2:10][C:9]1=[O:11])([CH3:3])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 12.752 g (35.6 mmol) of [4R,5R]-4,5-bis(((1,1-dimethylethyl)-dimethylsilyl)oxymethyl)-1-oxaspiro[2,2]pentane, from Step D, in 50 mL of methylene chloride was added to a solution of 3.814 g (28.5 mmol) of lithium iodide in 200 mL of methylene chloride which had been cooled in an ice bath. After stirring the reaction mixture for 1 h at 0° C., the ice bath was removed and the reaction mixture was stirred for 20 minutes at ambient temperature. The reaction mixture was then washed with 5% aqueous sodium bicarbonate solution, 5% sodium bisulfite solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 12.317 g (96.6% crude yield) of the title compound which was taken on to the next step without purifiaction; MS DCI-NH3M/Z: 376 (M+NH4)+.

Workup

temperaturehad been cooled in an ice bath
customthe ice bath was removed
stirringthe reaction mixture was stirred for 20 minutes at ambient temperature
washThe reaction mixture was then washed with 5% aqueous sodium bicarbonate solution, 5% sodium bisulfite solution and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7ec30e53b2a04dcaad75f537b4457fc2
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246931

Linked notes

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