Dichloromethane → Methyl 8-cyano-2-[(2,2-diethoxyethyl)sulfanyl]octanoate

HRID 918281Notes

Reaction equation

HRID 918281 reaction equation
Br[CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C:3]([O:5][CH3:6])=[O:4].[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][SH:20])[CH3:16].C(Cl)Cl>C(N(CC)CC)C>[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][S:20][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C:3]([O:5][CH3:6])=[O:4])[CH3:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 109426222,2-diethoxy-ethanethiolHCID 20364819Methyl 2-bromo-8-cyanooctanoate

Product 1

HCID 54422104Methyl 8-cyano-2-[(2,2-diethoxyethyl)sulfanyl]octanoate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The starting material is prepared as follows: To the mixture of 13.6 g of methyl 2-bromo-8-cyano-octanoate, 11.6 g of 2,2-diethoxy-ethylmercaptan and 150 ml of methylene chloride, 5.56 g of triethylamine are added dropwise while stirring. After overnight-stirring at room temperature the mixture is evaporated, the residue triturated with diethyl ether, washed with water, dried and evaporated, to yield the methyl 2-(2,2-diethoxyethylmercapto)-8-cyano-octanoate showing NMR bands aft 4.58, 3.71 and 2.75 ppm.

Workup

  1. customThe starting material is prepared
  2. additionare added dropwise
  3. stirringAfter overnight-stirring at room temperature the mixture
  4. customis evaporated
  5. customthe residue triturated with diethyl ether
  6. washwashed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-23b4ac682abb44bebb2a4f0dc7410030
Source dataset
uspto-grants-1976_07
Patent number
US03970670

Reaction notes

Loading…