Sodium Iodide → (4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane

HRID 1917505노트

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HRID 1917505 반응식
[CH3:1][C:2]1([CH3:10])[O:6][C@@H:5]([CH2:7][CH2:8]O)[CH2:4][O:3]1.C(N(CC)CC)C.CS(Cl)(=O)=O.[NH4+].[Cl-].[Na+].[I-:26]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CC(C)=O.O>[I:26][CH2:8][CH2:7][C@H:5]1[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]1

참가 물질

10

반응물 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 110518052-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

생성물 1

HCID 11076039(4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane수율 32%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 180Acetone용매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of (S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol (1.58 mL, 10.0 mmol) in CH2Cl2 (25 mL) was added DMAP (120 mg, 1.0 mmol) and triethylamine (2.08 mL, 15.0 mmol). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (12.0 mmol, 0.928 mL) was added slowly dropwise under N2 atmosphere. The reaction mixture was stirred for 2 h (monitored by TLC, 1:2 EtOAc—Hexanes). Saturated NH4Cl solution (20 mL) was added and the mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to provide a yellow oil, which was dissolved in dry acetone (25 ml), followed by addition of NaI (7.5 g, 50 mmol). The reaction mixture was refluxed for 2 h (monitored by TLC, 1:4 EtOAc—Hexanes), cooled to room temperature and water (50 mL) was added. Extraction with ethyl acetate, washing of the combined organic layers with brine, drying over anhydrous Na2SO4, filtration and concentration provided a yellow oil, which was purified by flash chromatography (25% EtOAC-Hexane) to afford the title compound, (S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane (0.82 g, 32% over two steps) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36 (s, 3H), 1.41 (s, 3H), 1.99-1.16 (m, 2H), 3.25 (dd, J=18.19, 8.84 Hz, 2H), 3.58 (t, J=7.20 Hz, 1H), 4.03-4.13 (m, 1H), 4.13-4.24 (m, 1H). MS (ES) [M+H] calculated for C2H14IO2, 257.00; found 257.08.

후처리

  1. extractionthe mixture was extracted with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a yellow oil, which
  7. temperaturecooled to room temperature
  8. extractionExtraction with ethyl acetate
  9. washwashing of the combined organic layers with brine
  10. dry with materialdrying over anhydrous Na2SO4, filtration and concentration
  11. customprovided a yellow oil, which
  12. customwas purified by flash chromatography (25% EtOAC-Hexane)

출처 및 근거

ORD 기록
ord-e8b2e08c9d4749739ba3d75b8b119e5d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618290B2

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