Ethyl 2-(chloromethyl)-1,4-dithiaspiro[4.5]decane-7-acetate → Ethyl 2-[(acetylthio)methyl]-1,4-dithiaspiro[4.5]decane-7-acetate

HRID 1608273Notes

Reaction equation

HRID 1608273 reaction equation
[C:1]([S:4][CH2:5][CH:6]1[CH2:10][S:9][C:8]2([CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]2)[S:7]1)(=[O:3])[CH3:2].Cl[CH2:22]C1CSC2(CCCC(CC(OCC)=O)C2)S1.C([O-])(=S)C.[K+]>CN(C=O)C>[C:1]([S:4][CH2:5][CH:6]1[CH2:10][S:9][C:8]2([CH2:14][CH2:13][CH2:22][CH:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]2)[S:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 19849015Ethyl 2-(chloromethyl)-1,4-dithiaspiro[4.5]decane-7-acetateHCID 19849041Ethyl 2-[(acetylthio)methyl]-1,4-dithiaspiro[4.4]nonane-7-acetateHCID 23670855Potassium ethanethioate

Product 1

HCID 19849016Ethyl 2-[(acetylthio)methyl]-1,4-dithiaspiro[4.5]decane-7-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The titled compound was synthesized according to the procedure used for the synthesis of the thioacetate of Example F using the chloride of Example H derived from the less polar pair of racemates (0.62 g, 0.002 mole) and potassium thioacetate (917 mg) in DMF (15 ml). The crude product was chromatographed on silica gel using 10% ethyl acetate/hexane to give 0.57 g of the titled product (Product A.)

Workup

  1. customThe titled compound was synthesized
  2. customThe crude product was chromatographed on silica gel using 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c9f9b30ea7584301bf93ff52a4846b2c
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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