Acetone → HCID 68685487, compound

HRID 1865484Notes

Reaction equation

HRID 1865484 reaction equation
[CH:1]1([CH:4]([OH:18])[C:5]2([C:16]#[N:17])[CH2:10][CH2:9][CH:8](SCC3CC3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.O[O:20][S:21]([O-:23])=O.[K+].[C:25](=O)([O-])[O-].[Na+].[Na+].[CH3:31][C:32]([CH3:34])=O>O>[CH:1]1([CH:4]([OH:18])[C:5]2([C:16]#[N:17])[CH2:10][CH2:9][CH:8]([S:21]([CH2:31][CH:32]3[CH2:34][CH2:25]3)(=[O:23])=[O:20])[CH2:7][CH2:6]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 10340Sodium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 68681091HCID 68681091, compound

Product 1

HCID 68685487HCID 68685487, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-(cyclopropyl-hydroxy-methyl)-4-cyclopropylmethylsulfanyl-cyclohexanecarbonitrile (1.93 g; 7.27 mmol) in acetone (15 ml) was added a slurry of oxone (13.4 g; 21.8 mmol) in water (10 ml). The mixture was heated at 60° C. for 1 hour then allowed to cool to room temperature. Water (50 ml) was added and the pH was adjusted to 7 with 2 M sodium carbonate solution. The mixture was extracted with EtOAc (80 ml) and DCM 950 ml). The combined organics were dried (MgSO4) and evaporated in vacuo to give the product as a white solid (1.9015 g). 1H NMR (400 MHz, DMSO): δ 5.36 (1H, d, J 5.0), 3.11-3.05 (3H, m), 2.78 (1H, dd, J 4.8, 7.8), 2.26-2.20 (1H, m), 2.14-2.08 (3H, m), 1.67-1.43 (4H, m), 1.08-0.84 (2H, m), 0.62-0.58 (2H, m), 0.53-0.49 (1H, m), 0.46-0.30 (5H, m). m/z=320 (M+Na+).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with EtOAc (80 ml) and DCM 950 ml)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-8d0ae6bc1fca44cd81f341544b5cb0ac
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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