Hydrochloric Acid → HCID 178443127, compound

HRID 1925762Notes

Reaction equation

HRID 1925762 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].C[O-].[Na+].[CH2:8](Br)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].Cl>CO.O>[CH2:21]([CH2:2][C:1]([OH:4])=[S:3])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8208Myristyl bromideHCID 10942334Sodium MethoxideHCID 178418634HCID 178418634, compound

Product 1

HCID 178443127HCID 178443127, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Thioacetic acid (3.32 g, 36.0 mmol) in MeOH (150 ml) was treated successively with NaOMe (25% in MeOH, 12 g, 0.08 mol) and tetradecyl bromide (10.0 g, 0.036 mol) and stirred vigorously at room temperature for 48 h. The mixture was poured into H2O, acidified to pH 2 (conc. HCl) and extracted with diethyl ether. Drying (MgSO4) and concentration in vacuo afforded a crude solid which was purified by flash column chromatography (FCC) (25% EtOAc in hexanes to 35% EtOAc in hexanes) to yield 3 as a colourless solid (8.6 g, 82%); m.p. 64-66° C. (lit. 65-67° C.); δH(300 M, CDCl3) 0.89 (t, 3H, J=6.7 Hz), 1.27 (m, 22H), 1.32 (m, 2H), 1.61 (m, 2H), 2.67 (t, 2H, J 7.4) and 3.28 (s, 2H); MS (FAB+) 289 (M+H)+, 288 M+; HRMS: Found M+0288.211823. Calc. for C16H32O2S: M+0288.212302.

Workup

  1. extractionextracted with diethyl ether
  2. customDrying
  3. concentration(MgSO4) and concentration in vacuo
  4. customafforded a crude solid which
  5. customwas purified by flash column chromatography (FCC) (25% EtOAc in hexanes to 35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cd5adfc530e24632b599e6853bf0bad7
Source dataset
uspto-grants-2012_05
Patent number
US08178713B2

Reaction notes

Loading…