Sodium hydride → HCID 19605261, compound

HRID 1603651Notes

Reaction equation

HRID 1603651 reaction equation
[CH2:1]([S:8][CH:9]1[NH:12][C:11](=[O:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:1]([S:8][CH:9]1[N:12]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11](=[O:13])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12709818(4-Iodobutyl)benzeneHCID 19605253HCID 19605253, compound

Product 1

HCID 19605261HCID 19605261, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution 4-(benzylthio)azetidin-2-one (1.1 g, 5.5 mmol) in dry THF (10 ml) was added dropwise over 10 minutes to a suspension of NaH (0.13 g, 5.6 mmol) in dry THF (5 ml) at -20° C. under a N2 atmosphere. A solution of 1-iodo-4-phenylbutane (1.4 g, 5.5 mmol) in dry THF (10 ml) was added dropwise over 10 minutes at -55° C. After stirring for 18 hours, the mixture was poured onto ice/water (50 g), filtered through hyflo, the THF evaporated under reduced pressure and the residue taken up in ethyl acetate. The solution was washed with brine (×2), dried (MgSO4), evaporated under reduced pressure to a yellow oil which was purified by flash chromatography on silica gel eluted with 5:1, 3:1 then 1:1 petroleun ether/ethyl acetate to give the product as a yellow oil (0.25 g, 14%). 1H NMR δ (CDCl3) 1.5 (4H, m, 2×CH2), 2.6 (2H, m, CH2Ph), 2.85, 3.2 (each 2H, m, H-3 & NCH2), 3.73 (2H, s, SCH2), 4.54 (1H, m, H-4), 7.2 (10H, m, 2×Ph--H)

Workup

  1. additionthe mixture was poured onto ice/water (50 g)
  2. filtrationfiltered through hyflo
  3. customthe THF evaporated under reduced pressure
  4. washThe solution was washed with brine (×2)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure to a yellow oil which
  7. customwas purified by flash chromatography on silica gel
  8. washeluted with 5:1, 3:1

Sources & evidence

ORD record
ord-0d821eb87dee43209886bb2860a69f69
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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