Water → 9-(Methoxymethyl)-9H-fluorene-9-methanol

HRID 2252521ノート

反応式

HRID 2252521 の反応式
O.[OH:2][CH2:3][C:4]1([CH2:17][OH:18])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.[CH3:19]I.[H-].[Na+]>C1COCC1>[CH3:19][O:2][CH2:3][C:4]1([CH2:17][OH:18])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3450229H-Fluorene-9,9-dimethanol

生成物 1

HCID 226391039-(Methoxymethyl)-9H-fluorene-9-methanol収率 62.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under nitrogen atmosphere and water-free conditions, to a reactor were added in succession 80 ml of THF, 22.6 g of 9,9-bis(hydroxymethyl)fluorene and 57 g of methyl iodide. After the reaction mixture was admixed homogeneously by stirring, 4.6 g of 52% NaH in mineral oil 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 methyl iodide 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, the ether solution was evaporated to dryness 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 methyl iodide 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. customthe ether solution was evaporated to dryness
  10. customto give 22.8 g of crude
  11. customThe crude was purified through column chromatography

出典と根拠

ORDレコード
ord-ced896cfe0f040deb274025d11fe7998
出典データセット
uspto-grants-2008_01
特許番号
US07323431B2

反応ノート

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