Hydrochloric Acid → Glycerol-1,3-ditosylate

HRID 1419522

반응식

HRID 1419522 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 753GlycerolHCID 73974-Toluenesulfonyl chloride

생성물 1

HCID 13709207Glycerol-1,3-ditosylate

시약·촉매·용매 1

HCID 1049Pyridine용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4dbf2c01d9e1449084c6e2bb0cf304f3
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886190

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