Triethylamine → 3-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylsulfanyl]-benzonitrile

HRID 2266998Notes

Reaction equation

HRID 2266998 reaction equation
CS(Cl)(=O)=O.[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([S:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[C:18]#[N:19])[CH:11]=[CH:12][CH:13]=1.C(N(CC)CC)C.[OH:30][C:31]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35](O)[CH:34]=[CH:33][C:32]=1[C:41](=[O:43])[CH3:42].C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl.CN(C)C=O.C(OCC)C>[C:41]([C:32]1[CH:33]=[CH:34][C:35]([O:6][CH2:7][C:8]2[CH:9]=[C:10]([S:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[CH:11]=[CH:12][CH:13]=2)=[C:36]([CH2:37][CH2:38][CH3:39])[C:31]=1[OH:30])(=[O:43])[CH3:42]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 685357363-(3-Hydroxymethyl-phenylsulfanyl)-benzonitrile

Product 1

HCID 685357773-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylsulfanyl]-benzonitrileYield 76%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonyl chloride (0.119 g, 1.04 mmol) to a solution of 3-(3-hydroxymethyl-phenylsulfanyl)-benzonitrile (0.250 g, 1.04 mmol) and triethylamine (0.210 g, 2.07 mmol) in dichloromethane (0.2 M). Stir for 1 h. Evaporate solvent. Dissolve the residue in N,N-dimethylformamide and add 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (0.201 g, 1.04 mmol). Add cesium carbonate (0.673 g, 2.07 mmol) and stir for 1 h at 60° C. Dilute the reaction mixture with diethyl ether and wash with water (3×). Purify the residue by flash chromatography, eluting with hexanes, ramping to 50% ethyl acetate/hexanes to elute the title compound (0.331 mg, 0.790 mmol, 76%): MS (m/z): 416 (M−1).

Workup

  1. washwash with water (3×)
  2. customPurify the residue by flash chromatography
  3. washeluting with hexanes

Sources & evidence

ORD record
ord-0ed54fb08aec4888af6e74af52b55078
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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