Butanal → HCID 76785645, compound
Reaction equation
[CH3:1][O:2][S:3]([CH2:6]P(OCC)(OCC)=O)(=[O:5])=[O:4].[Li][CH2:16][CH2:17][CH2:18][CH3:19].C(=O)CCC.O>C1COCC1.CCCCCC>[CH3:1][O:2][S:3]([CH:6]=[CH:16][CH2:17][CH2:18][CH3:19])(=[O:4])=[O:5]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
(Diethoxy-phosphoryl)-methanesulfonic acid methyl ester (150 mg, 0.61 mmol) is dissolved in THF (5.0 mL) and it is cooled down to −78° C. 1.6M nBuLi (0.46 mL, 0.73 mmol) in hexane is added into it dropwise. The mixture is stirred for 30 min at that temperature and Butyraldehyde (0.066 mL, 0.73 mmol) is added. Then mixture is gradually warmed up to room temperature in 3 hrs and the reaction is further stirred for 2 hr at room temperature. Then 30 mL of water is added and the mixture is extracted with EtOAc (3×50 mL). The organic layers are combined, dried and concentrated to give 100 mg (100%) of Pent-1-ene-1-sulfonic acid methyl ester.
Workup
- additionis added
- temperatureThen mixture is gradually warmed up to room temperature in 3 hrs
- extractionthe mixture is extracted with EtOAc (3×50 mL)
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-40a9922a9d9a489881ba2fc8578f083d
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150556B2
Reaction notes
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