Hydrochloric Acid → 4-Mercapto-1-Methyl-tetrahydrothiopyraniumtriflate

HRID 978600Notes

Reaction equation

[O-:1][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].C([S:12][CH:13]1[CH2:18][CH2:17][S+:16]([CH3:19])[CH2:15][CH2:14]1)(=O)C.[OH-].[Na+].Cl>>[O-:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[SH:12][CH:13]1[CH2:18][CH2:17][S+:16]([CH3:19])[CH2:15][CH2:14]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 867414894-Acetylthio-1-methyl-tetrahydrothiopyraniumtriflate

Product 1

HCID 867414874-Mercapto-1-Methyl-tetrahydrothiopyraniumtriflate

Procedure

A cold (ice bath) aqueous solution (4 mL) of 4-acetylthio-1-methyl-tetrahydrothiopyraniumtriflate* (500 mg, 1.47 mmol) was treated with a 1M NaOH solution (2 mL, 2 mmol). The mixture was stirred for ca. 1 h. until all the starting material had disappeared on TLC (reversed phase silica gel). The pH of the strongly basic solution was brought to pH 7.5 with 10% HCl. This thiol was used as such for the next coupling reaction with the enol phosphate.

Sources & evidence

ORD record: ord-37a5dc12a0d54766a7a1b38584c2e8b8
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04665169

Reaction notes

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