1-Hexanethiol → HCID 54204796, compound

HRID 1440512Notes

Reaction equation

HRID 1440512 reaction equation
[C:1]([O:6][CH3:7])(=O)[C@@H:2]([CH3:4])O.[S:8](OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[CH2:23](S)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CC#N>[CH3:7][O:6][C:1](=[S:8])[C@H:2]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:4]

Participants

5

Reactant 3

HCID 81061-HexanethiolHCID 67749Trifluoromethanesulfonic anhydrideHCID 637514(+)-Methyl lactate

Product 1

HCID 54204796HCID 54204796, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-Methyl lactate (0.587 g, 5.55 mmol) was treated as described in Example 5 with triflic anhydride (1.07 ml, 6.38 mmol) and TEA (0.89 ml, 6.39 mmol) in 11 ml of CH3CN. Hexanethiol (1.07 ml, 7.21 mmol) and TEA (1.01 ml, 7.21 mmol) were added and the workup described in Example 5 followed by purification by silica gel chromatography using 25 to 1 hexane to ethyl acetate as eluent gave (S)-methyl-2-hexylthiopropionate as a clear yellow oil (0.737 g, 3.61 mmol, 65%). [α]D =-128° (c=1, MeOH); 1N NMR δ3.69 (s, 3H), 3.36 (q, 1H, J=7.19 Hz), 2.54 (m, 2H), 1.60-1.17 (m, 8H), 1.39 (d, 3H, J=7.19 Hz), 0.84 (t, 3H, J=6.79 Hz); 13C NMR δ173.35, 51.85, 40.70, 31.23, 31.13, 29.11, 28.36, 22.36. 17.00, 13.81.

Workup

  1. customfollowed by purification by silica gel chromatography

Sources & evidence

ORD record
ord-c63f6aa99b1d41ccb6387fe20bb21328
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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