2-Bromoethanol → Ristianol

HRID 485064Notes

Reaction equation

HRID 485064 reaction equation
C[O-].[Na+].Br[CH2:5][CH2:6][OH:7].[N:8]1[CH:13]=[CH:12][C:11]([CH2:14][SH:15])=[CH:10][CH:9]=1>C(O)C>[OH:7][CH2:6][CH2:5][S:15][CH2:14][C:11]1[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 10942334Sodium MethoxideHCID 13092602Pyridin-4-ylmethanethiol

Product 1

HCID 54050RistianolYield 18.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium methoxide (361 mg., 6.7 mmoles) was dissolved in 15 ml. of ethanol and cooled in an ice-water bath. 2-Bromoethanol (760 mg., 6.08 mmoles) was added dropwise over 5 minutes, followed by the dropwise addition of 4-picolyl mercaptan (760 mg., 6.08 mmoles) in 5 ml. of ethanol. The reaction mixture was warmed to room temperature and stirred for 20 hours. Precipitated salts were removed by filtration and the filtrate evaporated to crude product, which was chromatographed on 20 g. of silica gel with chloroform and then 1% methanol in chloroform as eluant. The column was monitored by tlc (9:1 chloroform:ethanol, Rf 0.25). Clean product fractions were combined and evaporated to yield clear title product as an oil (186 mg.), having m/e 269 and pnmr/CDCl3 /TMS/delta: 8.63-8.42 (m, 2H), 7.38-7.18 (m, 2H), 3.73 (t, 2H), 3.72 (s, 2H), 2.89 (s, broad, 1 H) and 2.63 (t, 2H) ppm.

Workup

  1. customPrecipitated salts were removed by filtration
  2. customthe filtrate evaporated to crude product, which
  3. customwas chromatographed on 20 g
  4. customevaporated

Sources & evidence

ORD record
ord-59d8d504ca2149bb922e0d1147f51c4c
Source dataset
uspto-grants-1985_08
Patent number
US04535084

Reaction notes

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