Water → HCID 49782542, compound

HRID 402304Notes

Reaction equation

HRID 402304 reaction equation
[H-].[Na+].[C:3]1([CH3:20])[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:18]=[O:19])[CH:4]=1.Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O>CS(C)=O>[CH2:22]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([C:5]3[CH:4]=[C:3]([CH3:20])[CH:8]=[CH:7][CH:6]=3)=[CH:17][CH:16]=2)[C:12]([CH:18]=[O:19])=[CH:13]1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 4186285HCID 4186285, compound

Product 1

HCID 49782542HCID 49782542, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

NaH (60% in mineral oil dispersion, 6 mmol, 1.2 equiv.) was added to a stirred solution of aldehyde 8 (5 mmol, 1 equiv.) in anhydrous dimethylsulfoxide (DMSO) at room temperature. After 1 h of stirring at the same temperature, 1-bromooctane was added and the mixture stirred for another 3 h. Distilled water was added to the reaction mixture which was then extracted with CH2Cl2. The organic layer was washed with brine, dried (anhydrous Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography with EtOAc/hexane as eluting solvents as described in Section 5.4.1. Yield: 62%; 1 H NMR (300 MHz, CDCl3): δ 9.98 (s, 1 H), 8.53 (s, 1 H), 7.66 (s, 1 H), 7.57-7.46 (m, 3 H), 7.39-7.29 (m, 2 H), 7.13 (d, J=7.2H, 1 H), 4.1 (t, J=8.7 Hz, 2 H), 2.42 (s, 3 H), 1.86 (t, J=3 H), 1.29-1.24 (m, 10 H), 0.86 (t, J=6.6 Hz, 3 H); 13C NMR (75 MHz, CDCl3): δ 184.8, 143.7, 141.6, 138.9, 135.4, 135.1, 129.1, 128.9, 127.1, 119.3, 119.2, 118.5, 116.8, 111.6, 47.4, 32.7, 31.6, 29.6, 29.0, 26.7, 22.5, 14.0.

Workup

  1. additionwas added
  2. extractionwas then extracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried (anhydrous Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography with EtOAc/hexane
  7. washas eluting solvents

Sources & evidence

ORD record
ord-ce7f4e42d0c643dd95e0cb8d48a5f003
Source dataset
uspto-grants-2014_06
Patent number
US08742100B2

Reaction notes

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