Methyl iodide → 9-(Methoxymethyl)-9H-fluorene-9-methanol

HRID 2416159

反応式

HRID 2416159 の反応式
[OH:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.I[CH3:19].[H-].[Na+]>O1CCCC1>[CH3:19][O:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3450229H-Fluorene-9,9-dimethanol

生成物 1

HCID 226391039-(Methoxymethyl)-9H-fluorene-9-methanol収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under nitrogen atmosphere and anhydrous condition, to a reactor were added in succession 80 ml of tetrahydrofuran, 22.6 g (0.1 mol) of 9,9-bis(hydroxymethyl)fluorene and 57 g (0.4 mol) of iodomethane. After the reaction mixture was admixed homogeneously by stirring, 4.6 g of 52% NaH in mineral oil (0.1 mol) was added batch-wise over 2 hours at room temperature, Upon completing the addition, the reaction mixture was stirred for further 2 hours. The unreacted iodomethane was recovered by distillation. The remainder was diluted with 100 ml of water, and extracted twice using 100 ml of diethyl ether for each time. The combined diethyl ether extract was dried over anhydrous sodium sulfate. After drying, thee ether solution was evaporated to dry to give 22.8 g of crude. The crude was purified through column chromatography to give 14.9 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (yield 62%).

後処理

  1. additionthe addition
  2. stirringthe reaction mixture was stirred for further 2 hours
  3. distillationThe unreacted iodomethane was recovered by distillation
  4. additionThe remainder was diluted with 100 ml of water
  5. extractionextracted twice
  6. extractionThe combined diethyl ether extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customAfter drying
  9. customthee ether solution was evaporated
  10. customto dry
  11. customto give 22.8 g of crude
  12. customThe crude was purified through column chromatography

出典と根拠

ORDレコード
ord-d62ed08e665f431d83347205370dea20
出典データセット
uspto-grants-2004_11
特許番号
US06822109B2

関連ノート

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