4-Toluenesulfonyl chloride → (2,3-Dihydro-1-benzofuran-2-yl)methyl 4-methylbenzene-1-sulfonate

HRID 1866537Notes

Reaction equation

HRID 1866537 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH:13]1[CH2:21][OH:22]>N1C=CC=CC=1.C1CCCCC1>[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH:13]1[CH2:21][O:22][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2795428(2,3-Dihydro-1-benzofuran-2-yl)methanol

Product 1

HCID 14099474(2,3-Dihydro-1-benzofuran-2-yl)methyl 4-methylbenzene-1-sulfonateYield 79%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8078CyclohexaneSolvent

Procedure

p-Toluenesulphonyl chloride (26.7 g, 140 mmol) was added to a solution of (2,3-dihydro-benzofuran-2-yl)-methanol (preparation 96) (21 g, 140 mmol) in pyridine (400 mL) and the mixture was stirred at room temperature for 4 days. The reaction mixture was then concentrated in vacuo and the residue was azeotroped with toluene, diluted with ethyl acetate (500 mL) and washed with 2M hydrochloric acid (2×300 mL). The organic solution was dried over magnesium sulfate and concentrated in vacuo to give a brown oil. Trituration of the oil in cyclohexane then afforded the title compound as a white solid in 79% yield, 33.5 g. LRMS APCI m/z 305 [M+H]+

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was azeotroped with toluene
  3. additiondiluted with ethyl acetate (500 mL)
  4. washwashed with 2M hydrochloric acid (2×300 mL)
  5. dry with materialThe organic solution was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil

Sources & evidence

ORD record
ord-10317835fa494734a011455864e5c241
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

Loading…