4-Toluenesulfonyl chloride → HCID 86599740, compound

HRID 1799447Notes

Reaction equation

HRID 1799447 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][OH:30])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1>C(Cl)Cl>[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44]([O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:46])=[O:45])=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 59408054HCID 59408054, compound

Product 1

HCID 86599740HCID 86599740, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10 (1.06 g, 2.46 mmol) in 30 mL of CH2Cl2 was added triethylamine (0.62 mL, 4.45 mmol). 4-Toluenesulfonyl chloride (TsCl, 567 mg, 2.97 mmol) was added to this solution in one portion at 0° C., and the mixture was stirred at under Ar for 24 h allowing it to warm to room temperature slowly. The reaction was quenched by pouring into a mixture of water (100 mL) and chloroform (70 mL), separated organic layer, and the aqueous layer was further extracted with chloroform (100 mL). The combined organic layers were dried over sodium sulfate (Na2SO4) and concentrated. The crude product was chromatographed (SiO2, gradient, hexane/EtOAc 5:1 to 2:1) to give 1.08 g (1.85 mmol, 75%) of 11 as a clear colorless oil. Rf 0.65 (hexane/EtOAc 1:1); 1H NMR (400 MHz, CDCl3) 7.79 (d, 2H, J=8.3 Hz, H-2 of tosyl), 7.68 (m, 4H, H-2 of phenyl), 7.44-7.35 (m, 6H, H-3 and H-4 of phenyl), 7.32 (d, 2H, J=8.7 Hz, H-3 of tosyl), 4.14 (t, 2H, J=4.9 Hz, TsOCH2CH2), 3.80 (t, 2H, J=5.3 Hz, CH2OSi), 3.66 (t, 2H, J=4.9 Hz, TsOCH2CH2), 3.64-3.54 (m, 10H, (OCH2CH2)2OCH2CH2OSi), 2.43 (s, 3H, CH3 of tosyl), 1.04 (s, 9H, C(CH3)3); MS (ESI) Calcd for C31H42O7SSiNa (M+Na+): 609.2. Found: 609.2.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into a mixture of water (100 mL) and chloroform (70 mL)
  3. customseparated organic layer
  4. extractionthe aqueous layer was further extracted with chloroform (100 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was chromatographed (SiO2, gradient, hexane/EtOAc 5:1 to 2:1)

Sources & evidence

ORD record
ord-aa103bb3b6e64223afac787b978376cc
Source dataset
uspto-grants-2013_01
Patent number
US08344125B2

Reaction notes

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