Cesium carbonate → HCID 11392975, compound

HRID 1866487Notes

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:29])([O:26][CH2:27][CH3:28])[O:22][CH:23](Cl)[CH3:24]>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][CH:23]([O:22][C:21]([O:26][CH2:27][CH3:28])=[O:29])[CH3:24])=[O:18]

Participants

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. 1-Chloroethyl ethyl carbonate (0.61 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 (3×25 ml), dried with MgSO4 and filtered. Evaporation in vacuo gave the product as a colourless oil (0.96 g, 75.1%). 1H-NMR (CDCl3) δ 6.74 (q, 1H), 4.19 (q, 2H), 3.64 (s, 3H), 2.34-2.24 (m, 4H), 1.63-1.53 (m, 4H), 1.49 (d, 2H), 1.33-1.24 (m, 9H). 13C-NMR (CDCl3) δ 174.55, 172.04, 162.92, 153.39, 91.48, 64.75, 51.79, 36.85, 34.37, 31.78, 29.24, 25.19, 24.82, 19.09, 14.48.

Workup

temperatureThe reaction mixture was cooled to room temperature
customevaporated in vacuo
additionDiethyl ether (25 ml) was added
washthe residue was washed with saturated NaHCO3 (3×25 ml)
dry with materialdried with MgSO4
filtrationfiltered
customEvaporation in vacuo

Sources & evidence

ORD record: ord-68e8eaa9397a4d2daddb965d74e79fea
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629383B2

Reaction notes

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