Sodium hydride → HCID 10786964, compound

HRID 1358866Notes

Reaction equation

HRID 1358866 reaction equation
[H-].[Na+].[CH:3]([C:5]1[NH:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=1)=[O:4].[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O>>[C:21]([O:20][C:18]([N:6]1[CH:7]=[CH:8][C:9]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][CH:11]=2)=[C:5]1[CH:3]=[O:4])=[O:17])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 90495Di-tert-butyl dicarbonateHCID 10613913HCID 10613913, compound

Product 1

HCID 10786964HCID 10786964, compound

Procedure

Following a standard procedure (Tietze, L. F.; Kettschau, G.; Heitmann, K. Synthesis 1996, 851-857), sample of NaH (70 mg, 1.75 mmol, 60% dispersion in mineral oil) in a round-bottomed flask under argon was washed twice with anhydrous pentane (˜5 mL). Anhydrous THF (14 mL) was added followed by 5 (400 mg, 1.35 mmol). After stirring for 30 min at room temperature, (BOC)2O (325 mg, 1.5 mmol) was added and stirring was continued for another 2 h. The reaction was quenched with 50% satd. aq NH4Cl (50 mL). The mixture was extracted with ether, and the combined organic layers were washed with brine, dried (Na2SO4), and filtered [silica, hexanes/ethyl acetate (4:1)] to yield a viscous oil (535 mg, quantitative). 1H NMR δ1.64 (s, 9H), 6.33 (d, J=3.0 Hz, 1H), 7.30 (d, J=8.1 Hz, 2H), 7.46 (d, J=3.0 Hz, 1H), 7.72 (d, J=8.1 Hz, 2H), 10.22 (s, 1H); 13C NMR δ27.7, 85.8, 94.2, 113.2, 126.7, 128.5, 131.3, 132.8, 137.0, 137.4, 148.3, 181.6; FAB-MS obsd 397.0176, calcd 397.0175 (C16H16INO3).

Workup

  1. washwas washed twice with anhydrous pentane (˜5 mL)
  2. additionAnhydrous THF (14 mL) was added
  3. stirringstirring
  4. waitwas continued for another 2 h
  5. customThe reaction was quenched with 50%
  6. extractionThe mixture was extracted with ether
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered [silica, hexanes/ethyl acetate (4:1)]
  10. customto yield a viscous oil (535 mg, quantitative)

Sources & evidence

ORD record
ord-d86ac5f1f94d47d5a88ebba0eda02c98
Source dataset
uspto-grants-2003_07
Patent number
US06596935B2

Reaction notes

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