HCID 12813959、化合物 → HCID 12813967、化合物

HRID 1576238ノート

反応式

HRID 1576238 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]([CH3:25])[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=O>O1CCCC1>[OH:8][CH2:9][C:11]1([CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]([CH3:25])[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2

参加物

4

反応物 2

HCID 12813959HCID 12813959、化合物HCID 21226445Aluminium lithium hydride

生成物 1

HCID 12813967HCID 12813967、化合物収率 74.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

20 gm of lithium aluminum hydride were added over 15 minutes to iced 400 cc of tetrahydrofuran and then a solution of 36 gm of 9-methoxycarbonyl-9-(β-dimethylaminoethyl)-10-methyl-acridan in 400 cc of tetrahydrofuran was added thereto over 30 minutes. The mixture was refluxed for 2 hours, then refrigerated and 200 cc of tetrahydrofuran containing 20% water were added thereto at a temperature below 0°C. The mixture was filtered and the filtrate was washed with methylene chloride and distilled to dryness in vacuo. The residue was dissolved in methylene chloride and the organic phase was washed with water, dried over magnesium sulfate and concentrated while adding ethyl acetate to replace the methylene chloride. Crystallization started and after icing for one hour the mixture was filtered. The precipitate was washed with water and was dried to obtain 24.5 gm of 9-hydroxymethyl-9-(β-dimethylaminoethyl)-10-methyl-acridane melting at 150°C. Concentration of the mother liquor gave a second crop of 1.6 gm of the product for a total yield of 79%.

後処理

  1. temperatureThe mixture was refluxed for 2 hours
  2. customat a temperature below 0°C
  3. filtrationThe mixture was filtered
  4. washthe filtrate was washed with methylene chloride
  5. distillationdistilled to dryness in vacuo
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washthe organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. additionwhile adding ethyl acetate
  11. customCrystallization
  12. waitafter icing for one hour
  13. filtrationthe mixture was filtered
  14. washThe precipitate was washed with water
  15. customwas dried

出典と根拠

ORDレコード
ord-bf5bd0895c0247b3a59db9856ea5ef5d
出典データセット
uspto-grants-1976_09
特許番号
US03979515

反応ノート

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