Potassium Carbonate → HCID 58495670, compound

HRID 1190964Notes

Reaction equation

HRID 1190964 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][CH:4]([SH:8])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[C:16]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)#[N:17]>C(#N)C.O>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][CH:4]([S:8][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([C:16]#[N:17])=[CH:19][CH:20]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 58495652HCID 58495652, compound

Product 1

HCID 58495670HCID 58495670, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3,3-dimethylcyclohexanethiol (0.6 g, 4.16 mmol) in acetonitrile (50 mL) add potassium carbonate (1.72 g, 12.48 mmol) and stir at room temperature for 10 min. Add 4-cyanobenzyl bromide (816 mg, 4.16 mmol) and stir the suspension for 18 h. Dilute with water (50 mL) and extract with EtOAc (50 mL). Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1) to obtain the desired intermediate as a clear oil (0.4 g, 37%).

Workup

  1. extractionextract with EtOAc (50 mL)
  2. dry with materialDry the organic phase over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (10:1)

Sources & evidence

ORD record
ord-c2bebd78e90244e38b1fba28499e720c
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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