4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 4-(6-methoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl ester

HRID 397039Notes

Reaction equation

HRID 397039 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]1[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)=[O:4].[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.CCN(CC)CC>CC(C)=O>[CH3:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]([C:17]1[CH:18]=[CH:19][C:20]([O:23][S:32]([C:29]3[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=3)(=[O:34])=[O:33])=[CH:21][CH:22]=1)[N:5]([C:3](=[O:4])[C:2]([F:1])([F:24])[F:25])[CH2:14][CH2:13]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 120859392,2,2-trifluoro-1-[1-(4-hydroxyphenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethanone

Product 1

HCID 86583956Toluene-4-sulfonic acid 4-(6-methoxy-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl esterYield 115.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2,2,2-trifluoro-1-[1-(4-hydroxyphenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethanone (3.387 g, 9.64 mmol), p-toluenesulfonyl chloride (2.206 g, 11.6 mmol) and Et3N (1.6 ml, 11.6 mmol) in acetone (50 ml) was refluxed under N2 for 5 hr, then concentrated in vacuo. The remaining residue was suspended in H2O (100 ml) and extracted with CHCl3 (4×75 ml). The combined extracts were dried over MgSO4 and concentrated in vacuo to give 5.622 g of orange oil. Purification by flash chromatography, eluting with hexane:EtOAc (8:2) gave 4.383 g (90% yield) of white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with CHCl3 (4×75 ml)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-082367a376664279a05f2c2130a3b5bb
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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