Ethane, 2-bromo-1,1-diethoxy- → 4-(2,2-Diethoxyethylthiomethyl)pyridine

HRID 615593Notes

Reaction equation

HRID 615593 reaction equation
C[O-].[Na+].[N:4]1[CH:9]=[CH:8][C:7]([CH2:10][SH:11])=[CH:6][CH:5]=1.[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16]Br)[CH3:13]>C(O)C>[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16][S:11][CH2:10][C:7]1[CH:8]=[CH:9][N:4]=[CH:5][CH:6]=1)[CH3:13]

Participants

5

Reactant 3

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 10942334Sodium MethoxideHCID 13092602Pyridin-4-ylmethanethiol

Product 1

HCID 130926034-(2,2-Diethoxyethylthiomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Under a nitrogen atmosphere, sodium methoxide (0.60 g., 11 moles) is dissolved in approximately 15 ml. of stirring ethanol and cooled in an ice bath. 4-Picolyl mercaptan (1.4 g., 11 mmoles) in approximately 3 ml. of absolute ethanol is added over 5 minutes and the mixture stirred for 15 minutes. Bromoacetaldehyde diethylacetal (2.4 g., 11 mmoles) in approximately 15 ml. of absolute ethanol is then added over 5 minutes. The reaction mixture is warmed to room temperature and stirred for 16 hours. The reaction mixture is filtered and the filtrate evaporated to yield title product, which if desired, can be further purified by chromatography on silica gel.

Workup

  1. stirringstirred for 16 hours
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-caa855c264d64e71a12869e6c367f7c7
Source dataset
uspto-grants-1985_02
Patent number
US04500535

Reaction notes

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