4-Toluenesulfonyl chloride → HCID 18617757, compound

HRID 1264210Notes

Reaction equation

HRID 1264210 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14]O)=[CH:8][CH:7]=1.C(N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N-:36]=[N+:37]=[N-:38].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CN(C=O)C>[N:36]([CH2:14][CH2:13][C:12]([C:9]1[CH:10]=[CH:11][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][CH:8]=1)([CH3:17])[CH3:16])=[N+:37]=[N-:38]

Participants

9

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 33557Sodium AzideHCID 18617820HCID 18617820, compound

Product 1

HCID 18617757HCID 18617757, compoundYield 79.8%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

To a cooled solution (0° C.) of 3-(4-furan-2-yl-phenyl)-3-methyl-butan-1-ol (1.2 g, 5.2 mmol) (reference example 22) in CH2Cl2 (17 mL) is added triethylamine (0.86 mL, 6.2 mmol), p-toluenesulfonyl chloride (1.18 g, 6.2 mmol) and 4-dimethylaminopyridine (305 mg, 2.5 mmol). The resulting solution is allowed to warm to 20° C. while stirring for 1.5 h then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The residue is dissolved if DMF (17 mL), sodium azide (845 mg, 13 mmol) added and the mixture heated to 60° C. and stirred for 3 h. The mixture is cooled to 20° C., then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give 1.06 g of title compound as a colorless oil. 1H NMR (CDCl3) δ 1.36 (s, 6H), 1.95 (t, J=8 Hz, 2H), 3.03 (t, J=8 Hz, 2H), 6.46 (m, 1H), 6.62 (m, 1H), 7.34 (d, J=8 Hz, 2H), 7.46 (d, J=2 Hz, 1H), 7.62 (d, J=8 Hz, 2H). MS (ion spray) m/z 256 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. additionadded
  5. temperaturethe mixture heated to 60° C.
  6. stirringstirred for 3 h
  7. temperatureThe mixture is cooled to 20° C.
  8. washwashed with water and brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customThe residue is purified by flash chromatography (eluting with 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-59531715ba914c85abc3d419fd27d72b
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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