Sulfuryl chloride → ethyl 2-chloro-3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate

HRID 1530028Notes

Reaction equation

HRID 1530028 reaction equation
[O:1]=[C:2]([CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].S(Cl)([Cl:18])(=O)=O>C(OCC)C>[Cl:18][CH:3]([C:2](=[O:1])[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 23144053Ethyl 3-(oxan-4-yl)-3-oxopropanoate

Product 1

HCID 86649591ethyl 2-chloro-3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoateYield 85.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using ethyl 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate (1.0 g, 5.0 mmol), sulfuryl chloride (810 mg, 6.0 mmol) and diethyl ether (50 mL) as starting materials and in the same manner as in Example 20-B(i), the title compound (1.0 g, 85%) was obtained as a colorless oil.

Sources & evidence

ORD record
ord-e5c9befab57d4e378a404862bdd9a00f
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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