Boron trifluoride etherate → Ethyl 4-(mercaptomethyl)-2-methyl-1,3-dithiolane-2-propanoate

HRID 1650248Notes

Reaction equation

HRID 1650248 reaction equation
[SH:1][CH2:2][CH:3]([SH:6])[CH2:4][SH:5].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:8][CH2:9][C:10]([CH3:12])=O.B(F)(F)F.CCOCC>C(Cl)Cl>[SH:1][CH2:2][CH:3]1[CH2:4][S:5][C:10]([CH3:12])([CH2:9][CH2:8][C:7]([O:14][CH2:15][CH3:16])=[O:13])[S:6]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 10883Ethyl levulinateHCID 784951,2,3-Propanetrithiol

Product 1

HCID 14405950Ethyl 4-(mercaptomethyl)-2-methyl-1,3-dithiolane-2-propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure of Example 1 using 1,2,3-trimercaptopropane (5.6 g, 0.04 mol), ethyl levulinate (5.8 g, 0.04 mol) and boron trifluoride etherate (1.25 ml) in methylene chloride (150 ml). The crude product was chromatographed on silica gel using 5% ethyl acetate/hexane as eluent to give 3.35 g (31%) of product.

Workup

  1. customThe crude product was chromatographed on silica gel using 5% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-7cc069acdfad4109be4f3cc6cd629c36
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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