Pyridine → ((2S,4R)-4,5-diacetoxy-4-methyl-tetrahydrofuran-2-yl)methyl benzoate

HRID 409011

반응식

HRID 409011 반응식
[C:1]([O:9][CH2:10][C@H:11]1[O:18][CH:17]2[C@:13]([CH3:21])([O:14][C:15]([CH3:20])(C)[O:16]2)[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][C:23]([O:25]C(C)=O)=[O:24].N1C=CC=CC=1.[CH2-]C(C)=O>C(O)(=O)C.C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[C:1]([O:9][CH2:10][C@@H:11]1[CH2:12][C@:13]([O:25][C:23](=[O:24])[CH3:22])([CH3:21])[CH:17]([O:16][C:15](=[O:14])[CH3:20])[O:18]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 66778757((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methyl benzoateHCID 178477758HCID 178477758, 화합물

생성물 1

HCID 66779482((2S,4R)-4,5-diacetoxy-4-methyl-tetrahydrofuran-2-yl)methyl benzoate수율 88%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

A mixture of 3.8 g of ((5S,6aR)-2,2,6a-trimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5-yl)methyl benzoate (from step 9) in 25 mL of 70% acetic acid was heated to 70° C. for 48 h. The reaction mixture was diluted with ethyl acetate and washed with water and saturated NaHCO3. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Crude diol obtained was aceylated using Ac2O (0.03373 mol, 3.18 mL) and 20 mL of anhydrous pyridine with catalytic amount of DMAP (5 mol %). The progress of the reaction was monitored by TLC. Pyridine was removed under vacuum and the residue was diluted with ethyl acetate and was washed with 1N HCl and saturated NaHCO3. The organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Purified by column chromatography to give 3.3 g of the title compound (88% yield) and 0.55 g of starting material acetonide was recovered.

후처리

  1. washwashed with water and saturated NaHCO3
  2. dry with materialThe organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customCrude diol obtained
  6. customPyridine was removed under vacuum
  7. additionthe residue was diluted with ethyl acetate
  8. washwas washed with 1N HCl and saturated NaHCO3
  9. dry with materialThe organic layers were dried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurified by column chromatography

출처 및 근거

ORD 기록
ord-c11def04f66b48289510920811fe42b7
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759318B2

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