4-Toluenesulfonyl chloride → HCID 57890216, compound

HRID 1819970Notes

Reaction equation

HRID 1819970 reaction equation
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:18]2[S:22][C:21]([CH2:23][OH:24])=[C:20]([CH3:25])[CH:19]=2)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][C:8]=1[CH3:26])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1>CCOCC>[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:18]2[S:22][C:21]([CH2:23][O:24][S:42]([C:39]3[CH:40]=[CH:41][C:36]([CH3:46])=[CH:37][CH:38]=3)(=[O:44])=[O:43])=[C:20]([CH3:25])[CH:19]=2)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][C:8]=1[CH3:26])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 57890220HCID 57890220, compound

Product 1

HCID 57890216HCID 57890216, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophen-2-yl)-methanol (1.0 g, 2.39 mmol) in Et2O (5 ml) is added triethyl amine (666 μl, 4.78 mmol). The mixture is added to a solution of p-toluenesulfonyl chloride (501 mg, 2.62 mmol) in Et2O (5 ml) and stirred overnight. The reaction is filtered, concentrated and chromatographed (12 g SiO2, 5% EtOAc/Hex) to yield the title compound (740 mg, 55%).

Workup

  1. filtrationThe reaction is filtered
  2. concentrationconcentrated
  3. customchromatographed (12 g SiO2, 5% EtOAc/Hex)

Sources & evidence

ORD record
ord-cf6f250494b8469f87ffd02bfe9667da
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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