Potassium ethanethioate → HCID 131725745, compound

HRID 2111469Notes

Reaction equation

HRID 2111469 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C-:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)=[CH:5][CH:4]=1.[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19].[C:20]([O-:23])(=[S:22])[CH3:21].[K+]>CN(C=O)C>[C:20]([S:22][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C-:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)=[CH:5][CH:4]=1)(=[O:23])[CH3:21].[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 131725744HCID 131725744, compound

Product 1

HCID 131725745HCID 131725745, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Following a general procedure (Zhang et al. (1999) Tetrahedron Lett., 40: 603-606), a solution of 19 (1.5 g, 4.2 mmol) in DMF (10 mL) was added to a solution of potassium thioacetate (0.60 g, 5.0 mmol) in DMF (10 mL) and the mixture was stirred overnight at rt. The mixture was filtered and water was added to the filtrate. The filtrate was extracted with ethyl ether (3×50 mL), and the combined organic layers were dried (MgSO4) and evaporated in vacuo. The residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:1) affording a yellow solid (1.3 g, 90%): mp 79-81° C.; 1H NMR δ 2.38 (s, 3H), 4.05 (s, 5H), 4.12 (s, 2H), 4.31 (A2B2, J=1.5 Hz, 2H), 4.62 (A2B2, J=1.5 Hz, 2H), 7.21, 7.41 (AA′BB′, J=8.5 Hz, 2×2H); 13C NMR δ 31.1, 34.0, 67.2, 69.6, 70.3, 85.7, 127.0, 129.5, 135.7, 139.1, 196.1; FAB-MS obsd 350.0431, calcd exact mass 350.0428; Anal. Calcd for C19H18FeOS: C, 65.15; H, 5.18. Found: C, 64.91; H, 5.15.

Workup

  1. filtrationThe mixture was filtered
  2. additionwater was added to the filtrate
  3. extractionThe filtrate was extracted with ethyl ether (3×50 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography (silica, petroleum ether/diethyl ether, 10:1)

Sources & evidence

ORD record
ord-f2fb1fe402e5460e9f3617079d0d9bca
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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