4-Toluenesulfonyl chloride → HCID 86730908, compound

HRID 587126Notes

Reaction equation

HRID 587126 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH2:17][OH:18])([C:15]#[N:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C.CCOC(C)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:18][CH2:17][C:12]2([C:15]#[N:16])[CH2:13][CH2:14][CH:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:10][CH2:11]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 71239740HCID 71239740, compound

Product 1

HCID 86730908HCID 86730908, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(benzyloxy)-1-(hydroxymethyl)cyclohexanecarbonitrile (crude 770 mg, 1.0 equiv) in DCM (7 mL) was added p-toluenesulfonyl chloride (898 mg, 1.5 equiv), triethylamine (1.44 mL, 3.3 equiv) and DMAP (38 mg, 0.1 equiv). The solution was stirred at room temperature overnight. It was concentrated to give the residue. EtOAc (120 mL) was added. The organic solution was washed with saturated NaHCO3 (30 mL), H2O (30 mL) and HCl (1.0 N, 30 mL), brine (30 mL), dried over anhydrous Na2SO4 and then concentrated to give yellow solid which was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane: 0-30%) to afford 450 mg (yield 36%) of (4-(benzyloxy)-1-cyanocyclohexyl)methyl 4-methylbenzenesulfonate as a white solid.

Workup

  1. concentrationIt was concentrated
  2. customto give the residue
  3. washThe organic solution was washed with saturated NaHCO3 (30 mL), H2O (30 mL) and HCl (1.0 N, 30 mL), brine (30 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give yellow solid which
  7. customwas purified by CombiFlash (24 g silica gel column, EtOAc/Hexane: 0-30%)

Sources & evidence

ORD record
ord-13bd2df9edd24930b75ba90e0f78be1f
Source dataset
uspto-grants-2016_01
Patent number
US09226923B2

Reaction notes

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