Ethylene Oxide → 2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5-(2-hydroxyethyl)furan

HRID 2378406Notes

Reaction equation

[Li]C(C)(C)C.[CH3:6][C:7]([Si:10]([CH3:20])([CH3:19])[O:11][CH2:12][CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)([CH3:9])[CH3:8].[CH2:21]1[O:23][CH2:22]1.[NH4+].[Cl-]>C1COCC1>[CH3:9][C:7]([Si:10]([CH3:19])([CH3:20])[O:11][CH2:12][CH2:13][C:14]1[O:15][C:16]([CH2:21][CH2:22][OH:23])=[CH:17][CH:18]=1)([CH3:6])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

t-BuLi (1.2 M in pentane, 10 mL, 16.99 mmol) was added to a stirred solution of 255B (3.49 g, 15.44 mmol) in 13 mL of THF at −78° C. dropwise. The mixture was stirred for an additional 4 h at 0° C. Ethylene oxide (1.05 mL) was added at −78° C. to the reaction solution. The mixture was warmed to rt and stirred overnight. Aqueous sat. NH4Cl was added and most of the THF was removed under reduced pressure. The mixture was extracted with ether (3×) and the combined organic layers were washed with water (1×) and brine (1×) and dried over Na2SO4. Purification by flash chromatography on silica gel eluting with 5% EtOAc/95% CH2Cl2 gave 2.8 g (10.4 mmol, 67%) of compound 255C as a yellow oil.

Workup

temperatureThe mixture was warmed to rt
stirringstirred overnight
customwas removed under reduced pressure
extractionThe mixture was extracted with ether (3×)
washthe combined organic layers were washed with water (1×) and brine (1×)
dry with materialdried over Na2SO4
customPurification by flash chromatography on silica gel eluting with 5% EtOAc/95% CH2Cl2

Sources & evidence

ORD record: ord-0c03f7d529174ff7b2f19d048f926ced
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470797B2

Reaction notes

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