Hydrochloric Acid → Glycerol-1,3-ditosylate

HRID 2342

反応式

HRID 2342 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][CH:14]([CH2:16][OH:17])[OH:15].Cl>N1C=CC=CC=1>[S:7]([O:12][CH2:13][CH:14]([CH2:16][O:17][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[OH:15])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 753GlycerolHCID 73974-Toluenesulfonyl chloride

生成物 1

HCID 13709207Glycerol-1,3-ditosylate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

実験手順

Compound 2 was synthesized according to the previous reported method with modifications (Benbouzid et al., 1988). p-Toluenesulfonyl chloride (10.29 g, 54 mmol) dissolved in dry pyridine was added to a stirred solution of anhydrous glycerol (2.48 g, 27 mmol) in dry pyridine (30 ml at 0° C.). The solution was added slowly and left to react for 44 hours in the refrigerator (0°-3° C.). The pink mixture was poured over crushed ice and acidified with concentrated HCl. The organic layer was separated and the aqueous layer was washed with methylene chloride (2×50 ml). The combined organic extracts were washed successively with 2N HCl (2×10 ml) and distilled water (2×10 ml) and dried over anhydrous Na2SO4. The filtrate was evaporated and the residual crude product was purified by column chromatography on silica gel to afford Compound 2 as an oil: 9.72 g (24.3 mmol) yield 90%. 1H NMR [Chemical shift (d), multiplicity, coupling constant (Hz), number of protons, atom]: 7.75 (d; J=8.2 Hz; 4H, Har.); 7.35 (d; J=8.2 Hz; 4H; Har.); 4.1 (bs; 4H; H1,3); 3.35 (bs; 1H; H2); 2.4 (s; 6H; 2CH3). 13C NMR (ppm): 145 (C ar.); 131.7 (C ar.); 129.7 (CH ar.); 127.6 (CH ar.); 69.3 (C1,3); 66.7 (C2); 21.2 (CH3). Satisfactory 1H and 13C NMR data as well as mass spectral data were recorded for this compound. These spectra were consistent with the structures shown in FIG. 1.

後処理

  1. customCompound 2 was synthesized
  2. additionThe solution was added slowly
  3. waitleft
  4. customto react for 44 hours in the refrigerator (0°-3° C.)
  5. additionThe pink mixture was poured
  6. customover crushed ice
  7. customThe organic layer was separated
  8. washthe aqueous layer was washed with methylene chloride (2×50 ml)
  9. washThe combined organic extracts were washed successively with 2N HCl (2×10 ml)
  10. distillationdistilled water (2×10 ml)
  11. dry with materialdried over anhydrous Na2SO4
  12. customThe filtrate was evaporated
  13. customthe residual crude product was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-d183881774224975a1ab61e1760c6bad
出典データセット
uspto-grants-1998_03
特許番号
US05728843

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