4-Toluenesulfonyl chloride → HCID 22405677, compound

HRID 441080Notes

Reaction equation

HRID 441080 reaction equation
[O:1]=[C:2]1[C:5]([O:6][CH:7]([CH3:9])[CH3:8])=[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH:14]=[C:13]3[CH2:29][CH2:30][CH2:31][OH:32])[C:3]1=[O:33].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1.C(N(CC)CC)C.CCCCCC.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[O:1]=[C:2]1[C:5]([O:6][CH:7]([CH3:9])[CH3:8])=[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([Si:19]([CH:23]([CH3:24])[CH3:25])([CH:20]([CH3:21])[CH3:22])[CH:26]([CH3:28])[CH3:27])[CH:14]=[C:13]3[CH2:29][CH2:30][CH2:31][O:32][S:40]([C:37]2[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=2)(=[O:42])=[O:41])[C:3]1=[O:33]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 21226206Ethyl acetate hexaneHCID 22405678HCID 22405678, compound

Product 1

HCID 22405677HCID 22405677, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of 5-[1,2-dioxo-4-(1-methylethoxy)-3-cyclobuten-3-yl]-3-(3-hydroxypropyl]-1-triisopropylsilylindole (12) (0.208 g, 0.44 mmol) in 5 mL of dichloromethane was added p-toluenesulfonyl chloride (0.094 g, 0.49 mmol), followed by triethylamine (68 μL, 0.49 mmol) and a small but arbitrary amount of 4-dimethylaminopyridine. The cooling bath was then removed and the mixture was stirred at room temperature under Ar for 1 h. Another 0.047 g (0.25 mmol) of p-toluenesulfonyl chloride and 34 μL (0.24 mmol) of triethylamine were added and stirring was continued at room temperature for 18 h. The mixture was then diluted with dichloromethane, washed with 10% aqueous Na2CO3, dried (Na2SO4) and evaporated to give a yellow gum. Flash chromatography (SiO2 /CH2Cl2 then hexane-ethyl acetate, 1:1) of this material afforded the title compound (0.265 g, 97%) as a bright yellow gum: IR (neat) 1782, 1738, 1585, 1390 cm-1 ; 1H NMR (CDCl3, 400 MHz) δ 8.34 (d, J=1.5 Hz, 1H), 7.81 (dd, J=8.7, 1.5 Hz, 1H), 7.79 (d, J=8.3 Hz, 2H), 7.56 (d, J=8.7 Hz, 1H), 7.33 (d, J=8.0 Hz, 2H), 7.10 (s, 1H), 5.64 (hept, J=6.2 Hz, 1H), 4.09 (t, J=7.2 Hz, 2H), 2.87 (t, J=7.3 Hz, 2H), 2.44 (s, 3H), 2.11-2.05 (m, 2H), 1.70 (hept, J=7.5 Hz, 3H), 1.58 (d, J=6.1 Hz, 6H), 1.14 (d, J=7.5 Hz, 18H).

Workup

  1. customThe cooling bath was then removed
  2. stirringstirring
  3. waitwas continued at room temperature for 18 h
  4. washwashed with 10% aqueous Na2CO3
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give a yellow gum

Sources & evidence

ORD record
ord-2ce594e9f9f24d18b3f5b9fe76f05d9e
Source dataset
uspto-grants-1996_05
Patent number
US05521188

Reaction notes

Loading…