Iodine → (3aR,6aR)-5-iodo-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

HRID 470177노트

반응식

HRID 470177 반응식
[CH3:1][C:2]1([CH3:11])[O:6][CH:5]2[CH:7]=[CH:8][C:9](=[O:10])[CH:4]2[O:3]1.N1C=CC=CC=1.[I:18]I.O>C(Cl)Cl.C1COCC1>[I:18][C:8]1[C:9](=[O:10])[C@@H:4]2[O:3][C:2]([CH3:11])([CH3:1])[O:6][C@@H:5]2[CH:7]=1

참가 물질

7

반응물 4

HCID 807IodineHCID 962WaterHCID 1049PyridineHCID 137009922,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

생성물 1

HCID 15236394(3aR,6aR)-5-iodo-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

3aR,6aR)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (5-1) (1.2 g, 7.8 mmol, 1 equiv) was dissolved in DCM (50 mL) and pyridine (0.9 mL, 10.9 mmol, 1.4 equiv) was added followed by a solution of iodine (3.4 g, 13.2 mmol, 1.7 equiv) in THF (6 mL). The resulting mixture stirred overnight at ambient temperature. Upon disappearance of starting material, the reaction mixture was poured over water (30 mL), extracted with CHCl3 (3×50 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (80 g SiO2, 0-40% EtOAc in hexanes) to yield (3aR,6aR)-5-iodo-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (5-2) as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 7.97 (d, J=2.5 Hz, 1H); 5.22 (dd, J=5.5, 2.5 Hz, 1H); 4.53 (d, J=5.5 Hz, 1H); 1.42 (s, 3H); 1.39 (s, 3H).

후처리

  1. extractionextracted with CHCl3 (3×50 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography (80 g SiO2, 0-40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-35540e3064fd404eae55ba65e82ba561
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629275B2

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