Tetrahydrofuran → Fluoreneone

HRID 1743641

反応式

HRID 1743641 の反応式
[CH:1]1[C:13]2[C:12](=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4](C(Cl)=O)=[CH:3][CH:2]=1.S(C1C=CC(S)=CC=1)C1C=CC(S)=CC=1.C(N(CC)CC)C.[O:40]1CCCC1>>[C:1]1(=[O:40])[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 8471TriethylamineHCID 6101429-Fluorenone-4-carbonyl chlorideHCID 6194834,4'-Thiobisbenzenethiol

生成物 1

HCID 22281833Fluoreneone

実験手順

A 10.0 g of 9-fluorenone-4-carbonyl chloride (0.04 mole, obtained from Aldrich Chemicals Co, Milwaukee, Wis. 53201, USA) and 100 ml of tetrahydrofuran (obtained from Aldrich) were added to a 250 ml, 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The solution was stirred for about ½ hour, then 5.16 g of 4,4′-thiobisbenzenethiol (0.02 mole, obtained from Aldrich) in 50 ml of tetrahydrofuran were added, followed by the addition of 4.17 g of triethylamine (0.04 mole, obtained from Aldrich). The solution was refluxed for 6 hours and filtered hot to remove triethylamine hydrochloride salt byproduct. The filtrate was evaporated to dryness to obtain the crude product. The crude product was recrystallized from tetrahydrofuran/methanol with activated charcoal. The product was dried at 60° C. vacuum oven for 6 hours to yield a first dimeric fluorenone derivative, which was a yellow solid (6.85 g, 50% yield).

後処理

  1. customequipped with a reflux condenser and a mechanical stirrer
  2. temperatureThe solution was refluxed for 6 hours
  3. filtrationfiltered hot
  4. customto remove triethylamine hydrochloride salt byproduct
  5. customThe filtrate was evaporated to dryness
  6. customto obtain the crude product
  7. customThe crude product was recrystallized from tetrahydrofuran/methanol with activated charcoal
  8. customThe product was dried at 60° C. vacuum oven for 6 hours

出典と根拠

ORDレコード
ord-e8f4c99dce164634823dca4f396d7101
出典データセット
uspto-grants-2006_03
特許番号
US07011917B2

関連ノート

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