Sulfuric Acid → HCID 14849728, compound
Reaction equation
C([Li])CCC.C[Si]([C:10]([Si](C)(C)C)([C:14]([O-:16])=O)[C:11]([O-:13])=[O:12])(C)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])C(Cl)=O.C(=O)(O)[O-].[Na+].S(=O)(=O)(O)O>C1CCCCC1.CCOCC>[O:16]=[C:14]([C:25]1[CH:29]=[C:30]([O:34][CH3:35])[C:31]([O:32][CH3:33])=[C:23]([O:22][CH3:21])[CH:24]=1)[CH2:10][C:11]([OH:13])=[O:12]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
10 ml of 2M solution of n-butyllithium in cyclohexane was added dropwise over 10 minutes to a stirred solution of 5.08 g (20 mmol) of bis(trimethylsilyl)malonate in 40 ml of anhydrous ether under nitrogen atmosphere at −60° C. The mixture was then allowed to warm to 0° C. and the solution of 2.3 g (10 mmol) of 3,4,5-trimethoxybenzoyl chloride in 20 ml of anhydrous ethyl ether was added in one portion. The resulting mixture was stirred for 10 min. at 0° C. then shaken with 100 ml of 5% aqueous sodium bicarbonate for 5 minutes. The aqueous phase was acidified to pH=˜1 with cold 4N sulfuric acid and extracted with ethyl ether (3×100 ml). The combined extracts were dried over anhydrous magnesium sulfate, filtered off and evaporated to dryness to give the title compound as a creamy crystals (1.82 g, 71.6%); 1H NMR (CDCl3) δ 3.8-3.92 (m, 9H, OMe); 4.03 (s, 1.8 H, CH2); 5.62 (s, 0.2 H, CH enol); 7.2 (s, 2H, CH aromatic).
Workup
- extractionextracted with ethyl ether (3×100 ml)
- dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
- filtrationfiltered off
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-d2050917edd84a6daf2681811dead9fa
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198466B2
Reaction notes
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