Cesium carbonate → HCID 11324541, compound

HRID 1866486Notes

Reaction equation

HRID 1866486 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[CH3:7][O:8][C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].[C:21]([O:27][CH2:28]Cl)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>C1COCC1.[Na+].[I-]>[CH3:7][O:8][C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:28][O:27][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[O:18]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 75009Monomethyl azelateHCID 87885Chloromethyl pivalate

Product 1

HCID 11324541HCID 11324541, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A heterogeneous solution of Cs2CO3 (1.30 g, 4.0 mmol), NaI (30 mg, 0.20 mmol) and nonanedioic acid monomethyl ester (0.95 g, 4.0 mmol) in THF (15 ml) was stirred for ½ hour at 60° C. Chloromethyl pivalate (0.60 g, 4.0 mmol) in THF (5 ml) was added dropwise to the solution and stirred at 60° C. for 48 hours. The reaction mixture was cooled to room temperature and evaporated in vacuo. Diethyl ether (25 ml) was added, and the residue was washed with saturated NaHCO3 (3×15 ml), dried with MgSO4 and filtered. Evaporation in vacuo gave the product as a colourless oil (0.85 g, 67.5%). 1H-NMR (CDCl3) δ 5.74 (s, 2H), 3.66 (s, 3H), 2.38-2.26 (m, 4H), 1.63-1.56 (m, 4H), 1.31 (s, 6H), 1.21 (s, 9H). 13C-NMR (CDCl3) δ 177.05, 174.06, 172.23, 79.19, 51.33, 38.63, 33.90. 33.82, 28.78, 28.72, 28.64, 26.74, 24.73, 24.47.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customevaporated in vacuo
  3. additionDiethyl ether (25 ml) was added
  4. washthe residue was washed with saturated NaHCO3 (3×15 ml)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customEvaporation in vacuo

Sources & evidence

ORD record
ord-3cb740d1e22b495d992ba80a83774b63
Source dataset
uspto-grants-2009_12
Patent number
US07629383B2

Reaction notes

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