Octanoyl chloride → S-{3-[(Dimethoxymethyl)silyl]propyl} octanethioate

HRID 468218Notes

Reaction equation

HRID 468218 reaction equation
[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[SH:11][CH2:12][CH2:13][CH2:14][SiH2:15][CH:16]([O:19][CH3:20])[O:17][CH3:18].C(N(CC)CC)C>C1CCCCC1>[C:1]([S:11][CH2:12][CH2:13][CH2:14][SiH2:15][CH:16]([O:19][CH3:20])[O:17][CH3:18])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 169231HCID 169231, compound

Product 1

HCID 71417114S-{3-[(Dimethoxymethyl)silyl]propyl} octanethioateYield 96%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Octanoyl chloride (18.0 g, 0.111 mol) is added dropwise over 30 minutes to a solution of 3-mercaptopropyldimethoxymethylsilane F with CAS number [31001-77-1] (20.0 g, 0.111 mol) and triethylamine (11.2 g, 0.111 mol) in cyclohexane (200 mL) kept at 5° C. under an inert atmosphere. The temperature of the reaction medium remains between 5 and 8° C. The reaction medium is then stirred for 15 hours at room temperature. The precipitate of triethylamine hydrochloride Et3N.HCl is filtered over celite. After evaporating the solvents under reduced pressure at 25° C., S-octanoylmercaptopropyl-dimethoxymethylsilane G with CAS number [828241-23-2] (32.6 g, 0.106 mol) is obtained in the form of a colourless oil with a yield of 96%.

Workup

  1. customkept at 5° C. under an inert atmosphere
  2. customremains between 5 and 8° C
  3. filtrationThe precipitate of triethylamine hydrochloride Et3N.HCl is filtered over celite
  4. customAfter evaporating the solvents under reduced pressure at 25° C.

Sources & evidence

ORD record
ord-0afc97b9864346b7b160a8aa8e941d4e
Source dataset
uspto-grants-2014_01
Patent number
US08623937B2

Reaction notes

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