Diethyl Oxalate → HCID 131732554, compound

HRID 872928Notes

Reaction equation

HRID 872928 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.[C:18](OCC)(=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(OCC)C>[OH:24]/[C:18](=[C:13]1/[CH2:12][O:11][CH2:16][CH2:15][C:14]/1=[O:17])/[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 121599Tetrahydro-4H-pyran-4-oneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 131732554HCID 131732554, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-72 °C

Procedure

Lithium bis(trimethylsilyl)amide 1M solution (30.0 ml, 30.0 mmol) and diethyl ether (40 ml) were added into a flask under nitrogen atmosphere and cooled to −72° C. with dry ice/acetone-bath. Tetrahydro-4H-pyran-4-one (3 g, 30.0 mmol) was diluted with diethyl ether (10 ml) and added slowly to the previously cooled mixture. The resulting mixture was stirred at −70° C. for one hour. Diethyl oxalate (4.07 ml, 30.0 mmol) diluted with diethyl ether (10 ml) was added and the reaction mixture was allowed to warm to RT and stirred overnight. The formed yellow precipitate was filtered, washed with cold diethyl ether and dried with vacuum at 40° C. 1H-NMR (400 MHz; d6-DMSO): δ 1.16 (d, 3H), 1.92 (t, 2H), 3.68 (t, 2H), 3.98 (q, 2H), 4.19 (s, 2H).

Workup

  1. additionadded slowly to the previously cooled mixture
  2. additionwas added
  3. temperatureto warm to RT
  4. stirringstirred overnight
  5. filtrationThe formed yellow precipitate was filtered
  6. washwashed with cold diethyl ether
  7. customdried with vacuum at 40° C

Sources & evidence

ORD record
ord-65f254f91e8b4be6ab960aa2d8d73c15
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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