Octanoyl chloride → HCID 58534629, compound

HRID 1466968Notes

Reaction equation

HRID 1466968 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][Si:5]([CH3:10])([CH3:9])[O:6][CH2:7][CH3:8].C(N(CC)CC)C.[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1CCCCC1>[C:18]([S:1][CH2:2][CH2:3][CH2:4][Si:5]([O:6][CH2:7][CH3:8])([CH3:10])[CH3:9])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 222272273-[Ethoxy(dimethyl)silyl]propane-1-thiol

Product 1

HCID 58534629HCID 58534629, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Added dropwise at 5° C., under argon, to 3-mercaptopropyldimethylethoxysilane (34.0 g, 0.191 mol) in solution in triethylamine (19.2 g, 0.191 mol) and cyclohexane (400 ml) is octanoyl chloride (31.0 g, 0.191 mol) over 15 minutes at 8° C. The reaction medium is stirred for 15 hours at ambient temperature. The precipitate of triethylamine hydrochloride Et3N.HCl is filtered. The mixture obtained is purified by flash chromatography (eluent: petroleum ether, 500-600 ml). After evaporating the solvents under reduced pressure at 24° C., the S-octanoylmercaptopropylethoxydimethylsilane E with CAS number [1024594-66-8] (45.0 g, 0.148 mol) is obtained in the form of a colourless liquid with a yield of 78%.

Workup

  1. customover 15 minutes
  2. customat 8° C
  3. filtrationThe precipitate of triethylamine hydrochloride Et3N.HCl is filtered
  4. customThe mixture obtained
  5. customis purified by flash chromatography (eluent: petroleum ether, 500-600 ml)
  6. customAfter evaporating the solvents under reduced pressure at 24° C.

Sources & evidence

ORD record
ord-6051b65e13f149e1896952798bcf0927
Source dataset
uspto-grants-2015_04
Patent number
US09000092B2

Reaction notes

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