Trimethyl orthoformate → HCID 53419513, compound

HRID 1093094Notes

Reaction equation

HRID 1093094 reaction equation
O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].[CH:19]([O:24][CH3:25])([O:22][CH3:23])OC.O=[C:27]1C[CH2:30][CH:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:28]1>CCCCC>[CH3:25][O:24][C:19]1([O:22][CH3:23])[CH2:27][CH2:28][CH:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:30]1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 11355614Methyl 2-(3-oxocyclopentyl)acetateHCID 71586775Bentonite

Product 1

HCID 53419513HCID 53419513, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Tetrahedron, 57 (2001), 5183. A mixture of Montmorillonite K10 (188 g, 571 mmol) in trimethyl orthoformate (316 mL, 2856 mmol) was stirred for 2 hrs under nitrogen. To the mixture was slowly added methyl 2-(3-oxocyclopentyl)acetate (89.2 g, 571 mmol), as a suspension in pentane (500 mL). The mixture was stirred for 16 hrs, then filtered through a CELITE® pad rinsing with pentane. The filtrate was concentrated under reduced pressure to afford the title compound (104.9 g, 519 mmol, 91% yield) as an amber oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.67 (3 H, s) 3.20 (6 H, s) 2.35-2.46 (3 H, m) 2.11 (1 H, dd, J=13.18, 7.40 Hz) 1.86-1.96 (2 H, m) 1.74-1.83 (1 H, m) 1.44 (1 H, dd, J=13.05, 8.53 Hz) 1.34 (1 H, dd, J=12.55, 8.78 Hz). 13C NMR (101 MHz, CDCl3) δ ppm 172.73, 110.91, 50.93, 48.80, 48.61, 40.27, 39.66, 33.51, 33.25, 29.37.

Workup

  1. stirringThe mixture was stirred for 16 hrs
  2. filtrationfiltered through a CELITE® pad
  3. washrinsing with pentane
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7daed84b522a4d2a8101f39b4feb208f
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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