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

HRID 723665Notes

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-b13d61ce9ace4c8193a631097f620deb
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141578B2

Reaction notes

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