Imidazole → HCID 70976288, compound

HRID 2170730Notes

Reaction equation

HRID 2170730 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)[C:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.N1C=CN=C1.CN(C)C=O.[CH:34]([Si:37](Cl)([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])([CH3:36])[CH3:35]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=2)[C:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][O:11][Si:37]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])[CH:34]([CH3:36])[CH3:35])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 139400Triisopropylsilyl chlorideHCID 68272217HCID 68272217, compound

Product 1

HCID 70976288HCID 70976288, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(4-bromobenzyl)-5-(4-bromophenyl)-3,3-dimethylpentan-1-ol (0.974 g, 2.34 mmol) and 1,3-diaza-2,4-cyclopentadiene (0.351 g, 5.15 mmol) in a reaction container was deaerated, and the air inside the reaction container was replaced with argon. N,N-dimethylformamide (12 mL) and triisopropylsilyl chloride (0.68 g, 3.51 mmol) were then added to the mixed liquid. The thus obtained mixed liquid was stirred overnight at room temperature, and a sufficient amount of water was added to halt the reaction. The organic layer was separated from the mixed liquid, and the water layer was extracted with diethyl ether. The thus obtained organic layer was washed with a saturated saline solution and then dried using anhydrous magnesium sulfate. The organic layer was then filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:diethyl ether=50:1), yielding the title compound (4j) (1.16 g, 1.94 mmol) as a light yellow liquid in a yield of 83%.

Workup

  1. customThe thus obtained
  2. additionmixed liquid
  3. customthe reaction
  4. customThe organic layer was separated from the mixed liquid
  5. extractionthe water layer was extracted with diethyl ether
  6. washThe thus obtained organic layer was washed with a saturated saline solution
  7. customdried
  8. filtrationThe organic layer was then filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (hexane:diethyl ether=50:1)

Sources & evidence

ORD record
ord-fc4b5beb4d0042e4ad3c78752d94d10c
Source dataset
uspto-grants-2015_06
Patent number
US09051246B2

Reaction notes

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