Ethanol → HCID 67501552, compound

HRID 1625240Notes

Reaction equation

HRID 1625240 reaction equation
O[N:2]([CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[C:3]1[CH:11]=[C:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][C:20]([N:21]4[CH:25]=[C:24]([C:26]5[CH:27]=[N:28][N:29](CC6C=CC=CC=6)[CH:30]=5)[N:23]=[CH:22]4)=[C:15]3[C:14]([CH:38]([CH3:40])[CH3:39])=[N:13]2)[CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[O:6].C1CCCCC=1.C([OH:55])C>[OH-].[Pd+2].[OH-]>[NH:29]1[CH:30]=[C:26]([C:24]2[N:23]=[CH:22][N:21]([C:20]3[CH:19]=[CH:18][N:17]=[C:16]4[N:12]([C:10]5[CH:9]=[CH:8][C:4]([C:5]([NH2:7])=[O:6])=[C:3]([NH:2][CH:41]6[CH2:46][CH2:45][CH:44]([OH:55])[CH2:43][CH2:42]6)[CH:11]=5)[N:13]=[C:14]([CH:38]([CH3:39])[CH3:40])[C:15]=34)[CH:25]=2)[CH:27]=[N:28]1

Participants

5

Reactant 3

HCID 702EthanolHCID 8079CyclohexeneHCID 86664602HCID 86664602, compound

Product 1

HCID 67501552HCID 67501552, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Conditions

Temperature
80 °C

Procedure

Compound (93) (0.010 g) was dissolved in ethanol (1.0 mL). Palladium hydroxide (0.020 g) and cyclohexene (0.5 mL) were added to the resulting solution, followed by stirring under a nitrogen atmosphere at 80° C. for 24 hr. The reaction solution was filtered through celite, and the solvent was distilled away. The residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (95) (0.005 g, 56%) as a white solid.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. distillationthe solvent was distilled away
  3. customThe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-a9f886fd125145848ca9edd776c2a8c1
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

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