Sodium Methoxide → 5-(Azidomethyl)tetrahydro-3-thiophenethiol

HRID 1290398Notes

Reaction equation

HRID 1290398 reaction equation
[N:1]([CH2:4][CH:5]1[S:9][CH2:8][CH:7]([S:10]C(=O)C)[CH2:6]1)=[N+:2]=[N-:3].C[O-].[Na+]>CO>[N:1]([CH2:4][CH:5]1[S:9][CH2:8][CH:7]([SH:10])[CH2:6]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54464306Ethanethioic acid S-[5-(azidomethyl)tetrahydro-3-thienyl]ester

Product 1

HCID 189240395-(Azidomethyl)tetrahydro-3-thiophenethiolYield 20.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 0° C. solution, under argon, of 0.279 g of product from Example 141 in 3 ml of dry methyl alcohol is treated with 0.35 ml of 4.35M sodium methoxide. After 2 hours, the reaction mixture is concentrated in vacuo and the residue purified by chromatography (silica gel: 0-5% diethyl ether/hexane) to give 0.0465 g of the desired product.

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customthe residue purified by chromatography (silica gel: 0-5% diethyl ether/hexane)

Sources & evidence

ORD record
ord-90e8b35b34eb4995b566e18eb41e8d1b
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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