4-Toluenesulfonyl chloride → HCID 58380558, compound

HRID 1259412Notes

Reaction equation

HRID 1259412 reaction equation
[O:1]1[CH2:4][CH:3]([CH2:5][CH2:6][OH:7])[CH2:2]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:7][CH2:6][CH2:5][CH:3]2[CH2:4][O:1][CH2:2]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 108443452-(Oxetan-3-yl)ethan-1-ol

Product 1

HCID 58380558HCID 58380558, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using the same reaction conditions and procedure as described for the preparation of Intermediate (I-16a), 2-(oxetan-3-yl)ethanol (1 g, 6.944 mmol) was reacted with p-Toluene sulfonyl chloride (1.9 g, 10.416 mmol) in dry pyridine (10 mL) to afford the crude product. The reaction mass was poured into ice-water and extracted using ethyl acetate. The organic layer was washed with 1N HCl, brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (20% ethyl acetate in hexane) afforded 1 g of the product (40% yield).

Workup

  1. customthe same reaction conditions and procedure
  2. customto afford the crude product
  3. extractionextracted
  4. washThe organic layer was washed with 1N HCl, brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-25a6addfa0b04fc1b7f5f7ab3a18309c
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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