Hydrochloric Acid → HCID 86611129, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)([CH2:11][OH:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>C(Cl)Cl>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)([CH2:11][O:12][S:29]([CH3:28])(=[O:31])=[O:30])[C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH3:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A solution of 2-cyclohexylmethyl-2-hydroxymethyl-malonic acid diethyl ester (1.31 g, 4.13 mmol) in methylene chloride (20 mL) and triethyl amine (1.16 mL, 8.00 mmol) was cooled to −40° C. A solution of methylsulfonyl chloride (0.402 mL, 5.2 mmol) in methylene chloride (4 mL) was added to the reaction mixture over 5 minutes. The reaction mixture was warmed to −10° C. over 1 hour and then poured into cold dilute aqueous HCl. The product was extracted with ethyl acetate, the extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure to give 2-cyclohexylmethyl-2-methylsulfonyloxymethyl-malonic acid diethyl ester (1.505 g).
Workup
- extractionThe product was extracted with ethyl acetate
- washthe extracts were washed with saturated aqueous sodium chloride
- dry with materialdried over magnesium sulfate
- customThe solvent was removed by rotary evaporation at reduced pressure
Sources & evidence
- ORD record
- ord-54ccb370d9854cd5bc15905a3ba6b296
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07064123B1
Reaction notes
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