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

HRID 582833

反応式

HRID 582833 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 15337Mercuric acetate触媒HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-99ce5a5021e44c3c941cb9bb12988d89
出典データセット
uspto-grants-1999_07
特許番号
US05925770

関連ノート

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