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

HRID 1650259Notes

Reaction equation

HRID 1650259 reaction equation
[SH:1][CH2:2][CH:3]([SH:6])[CH2:4][SH:5].O=[CH:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].B(F)(F)F.CCOCC>C(Cl)Cl>[SH:1][CH2:2][CH:3]1[CH2:4][S:5][CH:8]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[S:6]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 784951,2,3-PropanetrithiolHCID 83779Methyl 4-oxobutyrate

Product 1

HCID 14405952Methyl 4-(mercaptomethyl)-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 (4.21 g, 0.03 mol), methyl 4-oxobutanoate from Example 73 (3.5 g, 0.03 mol) and boron trifluoride etherate (1 ml) in methylene chloride (75 ml). The crude product was chromatographed on silica gel using 5% ethyl acetate/hexane as eluent to give 2.5 g (35%) of product.

Workup

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

Sources & evidence

ORD record
ord-bcf38bee78c748e2937ac3d15f6b3e59
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

Loading…