Magnesium trifluoromethanesulfonate → (S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxypropanoate

HRID 1098168Notes

Reaction equation

HRID 1098168 reaction equation
FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=O.[O:18]1[CH2:20][C@H:19]1[C:21]([O:23][CH3:24])=[O:22].[Si:25]([O:42][CH2:43][CH2:44][OH:45])([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[Si:25]([O:42][CH2:43][CH2:44][O:45][CH2:20][C@H:19]([OH:18])[C:21]([O:23][CH3:24])=[O:22])([C:38]([CH3:40])([CH3:41])[CH3:39])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 2734125Magnesium trifluoromethanesulfonateHCID 10942355Methyl (2S)-2-oxiranecarboxylateHCID 151562692-((tert-Butyldiphenylsilyl)oxy)ethanol

Product 1

HCID 59279512(S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-hydroxypropanoateYield 43.1%

Conditions

Temperature
10 °C

Procedure

Magnesium trifluoromethanesulfonate (3.95 g, 12.24 mmol) was added in one portion to (S)-methyl oxirane-2-carboxylate (5 g, 48.98 mmol) and 2-(tert-butyldiphenylsilyloxy)ethanol (14.72 g, 48.98 mmol) at 10° C. The resulting suspension was stirred at 10° C. for 10 minutes and then warmed to 45° C. and stirred for 3 days. The crude product was purified by flash silica chromatography, eluting with 0 to 30% ethyl acetate in isohexane to afford the product (8.50 g, 43.1%). 1H NMR (400 MHz, CDCl3) δ 1.05 (9H, s), 3.10 (1H, d), 3.62 (2H, t), 3.74-3.87 (7H, m), 4.26-4.34 (1H, m), 7.35-7.46 (6H, m), 7.63-7.71 (4H, m); m/z (ESI+) (M+Na)+=425.37; HPLC tR=3.15 min.

Workup

  1. temperaturewarmed to 45° C.
  2. stirringstirred for 3 days
  3. customThe crude product was purified by flash silica chromatography
  4. washeluting with 0 to 30% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-5f1a0adf7bbc40d4928d05337bff140c
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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