1-Dodecanethiol → HCID 67032419, compound

HRID 920542Notes

Reaction equation

HRID 920542 reaction equation
C(S)CCCCCCCCCCC.CC([O-])(C)C.[K+].[CH2:20]([N:27]1[CH2:32][CH2:31][O:30][CH:29]([C:33]2[CH:38]=[CH:37][C:36]([O:39]C)=[CH:35][C:34]=2[Cl:41])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O>CN(C=O)C>[CH2:20]([N:27]1[CH2:32][CH2:31][O:30][CH:29]([C:33]2[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][C:34]=2[Cl:41])[CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 81951-DodecanethiolHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 67031671HCID 67031671, compound

Product 1

HCID 67032419HCID 67032419, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1 dodecanethiol (12.7 mL; 52.86 mmol) in dry DMF (50 mL), was added KOtBu (5.93 g; 52.86 mmol) at 0° C. After complete addition the mixture was allowed to slowly come to RT (˜30 min), and then 4-benzyl-2-(2-chloro-4-methoxy-phenyl)-morpholine (5.60 g; 17.62 mmol) was added. The resulting mixture was stirred at 110° C. for 6 hours. After cooling to RT, EtOAc was added and the resulting mixture was washed with 5% aqueous NaHCO3, water and brine; dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2CL2/MeOH 99:1) to afford 4-(4-benzyl-morpholin-2-yl)-3-chloro-phenol (4.56 g)

Workup

  1. additionAfter complete addition the mixture
  2. customto slowly come to RT
  3. custom(˜30 min)
  4. temperatureAfter cooling to RT
  5. washthe resulting mixture was washed with 5% aqueous NaHCO3, water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (SiO2, CH2CL2/MeOH 99:1)

Sources & evidence

ORD record
ord-70e75c9301354dbbae1f9220539fbba5
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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