Hydrochloric Acid → HCID 21968637, compound

HRID 1107869Notes

Reaction equation

HRID 1107869 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:11]([C@H:12]([OH:15])[CH2:13]O)=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].N1C=CC=CC=1.[S:22](Cl)([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23].Cl>CN(C1C=CC=CN=1)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.C(OCC)(=O)C>[CH3:1][C:2]1[O:3][C:4]2[C:11]([C@H:12]([OH:15])[CH2:13][S:22]([C:25]3[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 15407952HCID 15407952, compound

Product 1

HCID 21968637HCID 21968637, compoundYield 71.2%

Reagents, catalysts & solvents 3

HCID 73974-Toluenesulfonyl chlorideCatalystHCID 218852-DimethylaminopyridineCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

14 g (67.96 mmol) of (+)-2,3-dimethyl-7-(2-hydroxy-1(S)-hydroxyethyl)benzofuran and 250 ml of pyridine are introduced into a 500 ml three-necked flask. The mixture is cooled to 0° C. and 11.62 g (61.16 mmol) of tosyl chloride and then 0.5 g of dimethylaminopyridine are added. The reaction mixture is stirred for 2 h at room temperature, 0.645 g of tosyl chloride is added and stirring is continued for 16 h. The mixture is cooled to 0° C. and 300 ml of ethyl acetate and then 250 ml of a hydrochloric acid solution (4M) are added. Extraction is carried out with ethyl acetate (2×400 ml). The organic phases are combined, washed with 2×250 ml of a hydrochloric acid solution (4M), dried over magnesium sulphate and concentrated. The residue is purified by silica column chromatography (elution solvent: 25% ethyl acetate in cyclohexane). 15 g of (+)-2,3-dimethyl-7-(2-para-methylphenylsulphonyl-1(S)-hydroxyethyl)benzofuran are obtained in the form of a white solid--M.p.: 90° C.

Workup

  1. stirringstirring
  2. waitis continued for 16 h
  3. temperatureThe mixture is cooled to 0° C.
  4. extractionExtraction
  5. washwashed with 2×250 ml of a hydrochloric acid solution (4M)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue is purified by silica column chromatography (elution solvent: 25% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-1e0271642e0e4e9c82c889651c920cfb
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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