2-Mercaptoethanol → 2-[Methyl-bis(2-sulfanylethoxy) silyl]oxyethanethiol

HRID 64395Notes

Reaction equation

HRID 64395 reaction equation
C[Si:2]([CH3:11])([O:7][CH2:8][CH2:9][SH:10])[O:3][CH2:4][CH2:5][SH:6].C(N(CC)CC)C.ClC([SiH3])(Cl)Cl.[SH:24][CH2:25][CH2:26][OH:27]>CCOCC>[CH3:11][Si:2]([O:3][CH2:4][CH2:5][SH:6])([O:7][CH2:8][CH2:9][SH:10])[O:27][CH2:26][CH2:25][SH:24]

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 71317501CID 71317501HCID 716021552-[Dimethyl(2-sulfanylethoxy)silyl]oxyethanethiol

Product 1

HCID 867161632-[Methyl-bis(2-sulfanylethoxy) silyl]oxyethanethiol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The 2-[methyl-bis(2-sulfanylethoxy) silyl]oxyethanethiol (2) was synthesized according to the same procedure as 2-[dimethyl(2-sulfanylethoxy)silyl]oxyethanethiol (1), using triethylamine (8.08 g, 0.080 mol), trichloromethylsilane (3.98 g, 0.027 mol), and 2-mercaptoethanol (6.24 g, 0.080 mol) in ether (400 mL). 2-[methyl-bis(2-sulfanylethoxy) silyl]oxyethanethiol (2) was obtained as a clear, colorless, foul-smelling liquid (6.81 g, 93.2%). The product was purified by distillation under reduced pressure and obtained as a clear, colorless, foul-smelling liquid (4.53 g, 62.0%), Bp=128-129° C. at 0.25 mmHg.

Workup

  1. customThe 2-[methyl-bis(2-sulfanylethoxy) silyl]oxyethanethiol (2) was synthesized

Sources & evidence

ORD record
ord-c13c35ea8b6640a3b79618b51accddae
Source dataset
uspto-grants-2016_09
Patent number
US09447124B2

Reaction notes

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