Triethylamine → (R)-tert-Butyldimethyl(oxiran-2-ylmethoxy)silane

HRID 1371010Notes

Reaction equation

[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH2:16]1[O:18][C@H:17]1[CH2:19][OH:20]>C(Cl)Cl.CCOCC>[C:1]([Si:5]([CH3:7])([CH3:6])[O:20][CH2:19][C@H:17]1[CH2:16][O:18]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 23 °C

Procedure

tert-Butyl-chloro-dimethylsilane (12.9 g, 85.5 mmol) followed by Et3N (19 mL, 136 mmol) was added to a 0° C. solution of (S)-(+)-glycidol (5.0 g, 67 mmol) in CH2Cl2 (200 mL). The solution was allowed to warm to 23° C. with stirring over 17 h. The resulting pink solution was diluted with Et2O (800 mL) and stirred an additional 30 min. The Et2O layer was washed with saturated aqueous NaHCO3 (200 mL), H2O (2×100 mL), brine (100 mL), dried over Na2SO4 and concentrated. Purification by column chromatography (silica, 5-10% Et2O/hexanes) gave (R)-tert-Butyl-dimethyl-oxiranylmethoxy-silane (10.01 g, 79%). TLC (silica, 10% Et2O/hexanes): Rf=0.5. 1H NMR (CDCl3, 400 MHz): 3.85 (dd, J=11.9, 3.2 Hz, 1H), 3.66 (dd, J=11.9, 4.8 Hz, 1H), 3.09 (m, 1H), 2.77 (dd, J=5.0, 4.2 Hz, 1H), 2.64 (dd, J=5.2, 2.7 Hz, 1H), 0.90 (s, 9H), 0.08 (s, 3H), 0.07 (s, 3H).

Workup

stirringstirred an additional 30 min
washThe Et2O layer was washed with saturated aqueous NaHCO3 (200 mL), H2O (2×100 mL), brine (100 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customPurification by column chromatography (silica, 5-10% Et2O/hexanes)

Sources & evidence

ORD record: ord-9150266aee404d18b8c37ff32fc99d40
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583155B2

Reaction notes

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