Solketal → 5-[[(2,2-Dimethyl-1,3-dioxolan-4-yl)-methoxy]methyl]tetrahydro-2-furanmethanol

HRID 1278025

반응식

HRID 1278025 반응식
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].[CH2:12]1[O:14][CH:13]1[CH2:15][CH2:16][CH:17]1[O:19][CH2:18]1>O>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][CH2:18][CH:17]2[O:19][CH:13]([CH2:12][OH:14])[CH2:15][CH2:16]2)[CH2:4][O:3]1

참가 물질

5

반응물 3

HCID 7528SolketalHCID 159031,2:5,6-DiepoxyhexaneHCID 24758Sodium hydride

생성물 1

HCID 128887485-[[(2,2-Dimethyl-1,3-dioxolan-4-yl)-methoxy]methyl]tetrahydro-2-furanmethanol수율 58.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

46.3 g of 2,2-dimethyl-1,3-dioxolane-4-methanol (0.35 mol) (Aldrich) is cooled to 0° in an ice bath and under a nitrogen atmosphere 2.1 g of sodium hydride (0.088 mol) (washed with hexane to remove the mineral oil) is slowly added to the rapidly stirred mixture. The addition of the sodium hydride is made at such a rate that the temperature remains below 20°. After the addition of the NaH has been completed the mixture is allowed to stir for 1/2 hour and slowly warmed to room temperature. Slowly, and with stirring 10.0 g of 1,5-hexadiene diepoxide (0.088 mol) is added to the mixture. After the addition of the diepoxide has been completed the reaction mixture is heated at reflux for 16 hours. The mixture is then cooled to room temperature and with stirring is poured into 350 ml of water. The aqueous mixture is extracted with two 200 ml portions of chloroform, the CHCl3 extracts are combined and dried over anhydrous sodium sulfate. The CHCl3 is removed in vacuo and the dark brown residue then vacuum distilled through a 10 cm vigreux distilling column. The fraction boiling at 135°-137° @ 0.3 mm is collected yielding 12.6 g (58%) of the above compound.

후처리

  1. washwashed with hexane
  2. customto remove the mineral oil)
  3. additionis slowly added to the rapidly stirred mixture
  4. additionThe addition of the sodium hydride
  5. customremains below 20°
  6. additionAfter the addition of the NaH
  7. additionis added to the mixture
  8. additionAfter the addition of the diepoxide
  9. temperatureis heated
  10. temperatureat reflux for 16 hours
  11. temperatureThe mixture is then cooled to room temperature
  12. stirringwith stirring
  13. extractionThe aqueous mixture is extracted with two 200 ml portions of chloroform
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe CHCl3 is removed in vacuo
  16. distillationthe dark brown residue then vacuum distilled through a 10 cm
  17. distillationvigreux distilling column
  18. customThe fraction boiling at 135°-137° @ 0.3 mm is collected

출처 및 근거

ORD 기록
ord-6d4df769bad748f798d2d078e499b120
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04279902

연결된 노트

불러오는 중…