Ethanethiol → HCID 22808762, compound
Reaction equation
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]1[C@@H:18](/[CH:19]=[CH:20]/[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:17][CH2:16][C:15]1=[O:28]>C1COCC1>[CH2:1]([S:3][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]1[C@@H:18](/[CH:19]=[CH:20]/[CH2:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:17][CH2:16][C:15]1=[O:28])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl mercaptan (0.1 ml) was injected dropwise into a slurry of 1.0 ml THF and 62.5 mg of sodium hydride (50% in oil). The resultant slurry was stirred for 1.0 hour at 25° whereupon a solution of 167 mg 1-Bromo-16,20-methanoprost-13E-en-9-one in 1.0 ml of THF was injected and the reaction mixture was stirred for 3.0 hours at 25°. The reaction mixture was quenched by the addition of 10% aqueous HCl and extracted twice with chloroform. The chloroform extracts were washed with saturated aqueous NaHCO3 and then brine. They were dried (Na2SO4), filtered and evaporated in vacuo to yield 135 mg of an orange oil. The oil was chromatographed (85:15 silicic acid-Celite, benzene-ethyl acetate gradient elution) to afford 70.1 mg of a clear oil having the following structure: ##STR58## The structure of this material was confirmed by nuclear magnetic resonance and mass spectral analysis.
Workup
- customThe reaction mixture was quenched by the addition of 10% aqueous HCl
- extractionextracted twice with chloroform
- washThe chloroform extracts were washed with saturated aqueous NaHCO3
- dry with materialThey were dried (Na2SO4)
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-fa3511a6ce7c4e508d33a5d285252339
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04171331
Reaction notes
Loading…