Boron trifluoride etherate → Methyl 4-(mercaptomethyl)-2-methyl-1,3-dithiolane-2-butanoate

HRID 1383158Notes

Reaction equation

HRID 1383158 reaction equation
[SH:1][CH2:2][CH:3]([SH:6])[CH2:4][SH:5].[C:7]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=O)[CH3:8].B(F)(F)F.CCOCC>C(Cl)Cl>[SH:1][CH2:2][CH:3]1[CH2:4][S:5][C:7]([CH3:8])([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[S:6]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 784951,2,3-PropanetrithiolHCID 84129Methyl 5-oxohexanoate

Product 1

HCID 14405951Methyl 4-(mercaptomethyl)-2-methyl-1,3-dithiolane-2-butanoate

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 g, 0.0355 mol), methyl 4-acetylbutyrate (5.1 g, 0.0355 mol) and boron trifluoride etherate (1 ml) in methylene chloride (125 ml). The crude product was chromatographed on silica gel using 5% ethyl acetate/hexane as eluent to give 6.5 g (69%) of product.

Workup

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

Sources & evidence

ORD record
ord-c75bfbe022f043d29a563a1aa62ee253
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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