Dichloromethane → 3-Butynyl p-toluenesulfonate

HRID 1384043Notes

Reaction equation

HRID 1384043 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:12])[CH2:9][C:10]#[CH:11].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(Cl)Cl>C(OCC)(=O)C>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:12][CH2:8][CH2:9][C:10]#[CH:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 135663-Butyn-1-OL

Product 1

HCID 2720203-Butynyl p-toluenesulfonateYield 101.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (12.2 mL) was added dropwise to a mixture of 3-butyn-1-ol (5.09 g) and 4-toluenesulfonyl chloride (16.95 g) in 50 nm of CH2Cl2 cooled by an ice bath. The mixture was allowed to warm to room temperature. After 21 hours, the mixture was poured into ethyl acetate (150 mL) and washed with 0.1M HCl (75 mL), saturated NaHCO3 (75 mL), and brine (75 mL) and the organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. Purification by flash chromatography (10% ethyl acetate/hexane) gave 16.57 g of the product as a colorless solid.

Workup

  1. temperaturecooled by an ice bath
  2. washwashed with 0.1M HCl (75 mL), saturated NaHCO3 (75 mL), and brine (75 mL)
  3. dry with materialthe organic phase was dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5fef691bfe3b4cd4b286937c3dae08cf
Source dataset
uspto-grants-2001_07
Patent number
US06258360B1

Reaction notes

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