Iodine → HCID 178443479, compound

HRID 1440516Notes

Reaction equation

HRID 1440516 reaction equation
C[O:2][C:3](=[S:19])[C@@H:4]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C[Si](C)(C)[Si](C)(C)C.II>C(Cl)Cl>[CH2:13]([C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3]([OH:2])=[S:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 807IodineHCID 74057HexamethyldisilaneHCID 18656172(S)-methyl-2-hexylthiodecanoate

Product 1

HCID 178443479HCID 178443479, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
55 °C

Procedure

Alternatively, (S)-Methyl-2-hexylthiodecanoate (5.092 g, 16.8 mmol) was dissolved in methylene chloride (51 mL). To this solution was added hexamethyldisilane (5.4 mL, 26.4 mmol) and iodine (8.97 g, 35.3 mmol). The reaction was heated to 55° C. slowly and allowed to reflux for 2 hours. The reaction was cooled to rt and extracted with ethyl acetate (200 mL). The organic phase was washed with H2O (100 mL) followed by 0.1 N sodium bisulfite solution (2×200 mL) and brine. The organic phase was dried (MgSO4) and concentrated to yield (S)-2-hexylthiodecanoic acid (4.66 g, 16.15 mmol, 96%). [α]D =-49.7° (c=1.0, MeOH).

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureThe reaction was cooled to rt
  3. extractionextracted with ethyl acetate (200 mL)
  4. washThe organic phase was washed with H2O (100 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0856d9b3589a4db8b57d423fb0504be7
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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