Pyridine → HCID 13197283, compound

HRID 1777519Notes

Reaction equation

HRID 1777519 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH2:5][CH2:6][OH:7].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.N1C=CC=CC=1>ClCCl>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:7][CH2:6][CH2:5][C:4]#[C:3][Si:2]([CH3:9])([CH3:8])[CH3:1])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 27608274-Trimethylsilyl-3-butyn-1-ol

Product 1

HCID 13197283HCID 13197283, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(trimethylsilyl)but-3-yn-1-ol (1.00 mL; 6.00 mmol), 4-methylbenzene-1-sulfonyl chloride (2.29 g; 12.01 mmol), pyridine (0.970 mL; 12.00 mmol) in dichloromethane (15 mL) was stirred at room temperature for 60 hours. The reaction mixture was washed with an aqueous solution of saturated ammonium chloride, dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to yield 1.38 g (76%) of 4-(trimethylsilyl)but-3-ynyl 4-methylbenzenesulfonate.

Workup

  1. washThe reaction mixture was washed with an aqueous solution of saturated ammonium chloride
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-90061fd23b8040e9bbfa423519fa48f8
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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