Sodium Iodide → Selachyl alcohol

HRID 496992

반응식

HRID 496992 반응식
[H-].[Na+].[Na+].[I-].C[C:6]1([CH3:13])[O:10][CH:9]([CH2:11][OH:12])[CH2:8][O:7]1.S(C1C=CC(C)=CC=1)(O[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]CC)(=O)=O>CN(C=O)C.O>[CH2:6]([O:7][CH2:8][CH:9]([CH2:11][OH:12])[OH:10])[CH2:13][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 7528SolketalHCID 24758Sodium hydrideHCID 11258749Oleyl p-toluenesulfonate2회

생성물 1

HCID 5282282Selachyl alcohol

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of NaH (4.8 g, 120 mmol) and NaI (0.2 g) in dry DMF (20 mL) was added solketal (5.0 mL, 40 mmol) dropwise over a 30 min period. Once the effervescence had stopped, oleyl tosylate (Compound 13) (16.9 g, 40 mmol) was added and the reaction mixture was left for 3 days at 50° C. Then, H2O (10 mL) was added and the mixture was extracted with diethyl ether (2×100 mL), the combined organic phases were dried (MgSO4) and evaporated to dryness. The residue was taken up in THF (150 mL), 2M HCl was added until the solution turned turbid and the reaction was left to stir for 16 hours. The mixture was concentrated and subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 50/50, v/v] to give 1-O-oleyl-rac-glycerol (Compound 20) as an oil.

후처리

  1. extractionthe mixture was extracted with diethyl ether (2×100 mL)
  2. dry with materialthe combined organic phases were dried (MgSO4)
  3. customevaporated to dryness
  4. addition2M HCl was added until the solution
  5. waitthe reaction was left
  6. concentrationThe mixture was concentrated

출처 및 근거

ORD 기록
ord-d585c376d5b54cdf94295f6c69d773c9
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949529B2

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