Triethylamine → HCID 57656632, compound

HRID 2041518Notes

Reaction equation

HRID 2041518 reaction equation
[CH:1]1([CH:7]([OH:16])[C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C([O-])(O)=O.[Na+]>ClCCl.O>[CH:1]1([CH:7]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])[C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 118308504-(Cyclohexyl-hydroxy-methyl)-benzonitrile

Product 1

HCID 57656632HCID 57656632, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-(cyclohexyl-hydroxy-methyl)-benzonitrile (1 g, 4.66 mmol), and triethylamine (1.3 mL, 9.3 mmol) in dichloromethane (20 mL). Cool the mixture to 0° C., add methanesulfonyl chloride (1.49 mL, 5.34 mmol) and stir the solution for 2 h at 0° C. Add water (10 mL) and saturated aqueous NaHCO3 (10 mL). Separate the layers and extract back the aqueous phase with dichloromethane (3×20 mL). Combine the organic layers, wash with water (20 mL), dry over Na2SO4, filter and concentrate in vacuo to provide the desired intermediate as a yellow oil (1.29 g, 94%). MS (APCI) m/z: 294 (M+H)+.

Workup

  1. customSeparate the layers
  2. extractionextract back the aqueous phase with dichloromethane (3×20 mL)
  3. washCombine the organic layers, wash with water (20 mL)
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-3d7cb492cf3b4b839445cfe2c7f9dc41
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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