Hydrochloric Acid → HCID 178443124, compound

HRID 1925765Notes

Reaction equation

HRID 1925765 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].C[O-].[Na+].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>CO.O>[CH2:9]([CH2:2][C:1]([OH:4])=[S:3])[CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 58641109Cis-1-Bromo-tetradec-6-eneHCID 178418634HCID 178418634, compound

Product 1

HCID 178443124HCID 178443124, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Thioacetic acid (35 mg, 0.38 mmol) in methanol (20 ml) was treated successively with sodium methoxide (50 mg, 0.9144 mmol) and bromide 8 (105 mg, 0.381 mmol) and stirred at r.t. for 2 d. The reaction mixture was diluted in water and acidified with cold conc. aq. HCl. The aqueous layer was extracted with hexanes, dried (MgSO4) and concentrated invacuo to afford a crude residue was purified by flash column chromatography (eluent gradient elution 65-75% EtOAc in Hexanes) to afford the pure 4 as a viscous oil (105 mg, 0.367 mmol, 96%); δH(270 MHz, CDCl3); 0.86 (3H, t, J 6.8), 1.35 (14H, m), 1.60 (2H, m), 2.00 (4H, m), 2.65 (21, t, J 7.4), 3.24 (2H, s), 5.34 (2H, m) and 10.0 (1H, br s); δC(67.5 MHz, CDCl3) 14.20, 22.76, 27.09, 27.31, 28.45, 28.89, 29.32, 29.35, 29.35, 29.83, 31.95, 32.82, 33.54, 129.44, 130.36 and 176.77; MS (CI) 304 (M+NH4)+; HRMS: Found [M+NH4]+ 304.230876. Calc. for C16H34NO2S: [M+NH4]+0304.231026.

Workup

  1. extractionThe aqueous layer was extracted with hexanes
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated invacuo
  4. customto afford a crude residue
  5. customwas purified by flash column chromatography (eluent gradient elution 65-75% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-e8f8c06a6fd242d6acca8cec60e36f8c
Source dataset
uspto-grants-2012_05
Patent number
US08178713B2

Reaction notes

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