Oxalic acid dihydrate → HCID 86731005, compound

HRID 1852424Notes

Reaction equation

HRID 1852424 reaction equation
O.O.C(O)(=O)C(O)=O.C[O:10][CH:11]=[C:12]1[CH2:15][CH:14]([C:16]([OH:19])([CH3:18])[CH3:17])[CH2:13]1.C([O-])(O)=O.[Na+]>C1COCC1.O>[OH:19][C:16]([CH:14]1[CH2:15][CH:12]([CH:11]=[O:10])[CH2:13]1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 61373Oxalic acid dihydrateHCID 516892Sodium BicarbonateHCID 86731006HCID 86731006, compound

Product 1

HCID 86731005HCID 86731005, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Oxalic acid dihydrate (68 g, 0.54 mol) was added to a solution of 2-[3-(methoxymethylidene)cyclobutyl]propan-2-ol (70 g, 0.45 mol) in THF:H2O (1:1, 700 mL) at 0° C. and stirred at ambient temperature for 1 hour. Then, 10% aqueous NaHCO3 solution was added to the reaction mixture and extracted with EtOAc (500 mL×4). The combined organic layer was then washed with water (200 mL×2), brine (200 mL) dried over anhydrous Na2SO4 and concentrated in vacuo to afford the title compound as a pale yellow liquid (mixture of cis and trans isomers). 1H NMR (400 MHz, CDCl3, mixture of cis and trans): δ 1.09-1.11 (2 s, 6H), 2.07-2.26 (m, 4H), 2.31-2.39 (m, 1H), 2.95-2.99 (m, 1H), 9.75 & 9.84 (2 s, 1H). 13C NMR (100 MHz, CDCl3, mixture of cis and trans): δ 21.8, 26.1, 39.4, 40.7, 41.8, 70.3, 202.6. 1H NMR (400 MHz, DMSO-d6, mixture of cis and trans): δ 0.96 (s, 3H), 0.98 (s, 3H), 1.88-2.29 (m, 5H), 2.87-2.92 (m, 1H), 4.13 & 4.21 (2 s, 1H), 9.56 & 9.74 (2 s, 1H). 13C NMR (100 MHz, DMSO-d6, mixture of cis and trans): 22.1, 22.7, 26.8, 40.9, 41.9, 42.4, 68.8, 69.1, 203.8, 204.1. 1H NMR (400 MHz, DMSO-d6-D2O exchange, mixture of cis and trans): δ 0.94 (s, 3H), 0.96 (s, 3H), 1.85-2.22 (m, 5H), 2.86-2.90 (m, 1H), 9.53 & 9.71 (2 s, 1H).

Workup

  1. extractionextracted with EtOAc (500 mL×4)
  2. washThe combined organic layer was then washed with water (200 mL×2), brine (200 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a44443b3720d41a2aa49be06a4827d8f
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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