Sodium Chloride → 1,4-Dioxaspiro[4.6]undecan-7-ol

HRID 904

반응식

HRID 904 반응식
[O:1]1CCCC1.[CH2:6]1[O:16][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH:10]2)[O:8][CH2:7]1.[BH4-].[Na+].[Cl-].[Na+]>O.[OH-].[Na+].C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH2:7]1[O:8][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([OH:1])[CH2:10]2)[O:16][CH2:6]1

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 2794811,4-Dioxaspiro(4.6)undec-6-eneHCID 4311764Sodium borohydride

생성물 1

HCID 132988111,4-Dioxaspiro[4.6]undecan-7-ol

시약·촉매·용매 3

HCID 15337Mercuric acetate촉매HCID 962Water용매HCID 14798Sodium Hydroxide용매2회

실험 절차

Mercury(II) acetate (80.7 g, 0.25 mol) was dissolved in water (150 mL), then tetrahydrofuran (150 mL) was added to give a suspension. To this stirring suspension was added 2-cycloheptenone ethylene ketal (39 g, 0.25 mol). After stirring at ambient temperature for 3 hours, the mixture was cooled in an ice water bath. A 10% aqueous sodium hydroxide solution (150 mL) was added, followed by a solution of sodium borohydride (4.8 g, 0.13 mol) in 10% aqueous sodium hydroxide (150 mL). The mixture was allowed to reach ambient temperature and stirred overnight. The mixture was saturated with sodium chloride, stirred for 30 minutes, then allowed to settle; the solution was decanted into brine and extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo to give 3-hydroxycycloheptanone ethylene ketal (36 g).

후처리

  1. customto give a suspension
  2. temperaturethe mixture was cooled in an ice water bath
  3. customto reach ambient temperature
  4. stirringstirred overnight
  5. stirringstirred for 30 minutes
  6. customthe solution was decanted into brine
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-02e021bf3546479584ca183e01838f59
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723462

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