Tetrahydrofuran → 1,3-Diphenyl-2-propyn-1-one

HRID 6491

反応式

HRID 6491 の反応式
C([N-]C(C)C)(C)C.[Li+].O1CCCC1.[C:14]1([C:20]#[CH:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CON(C)[C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1CCCCC1>[C:26]1([C:25](=[O:32])[C:21]#[C:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 569575N-Methoxy-N-methylbenzamideHCID 2724682Lithium diisopropylamide

生成物 1

HCID 976371,3-Diphenyl-2-propyn-1-one収率 61.4%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

実験手順

Place lithium diisopropylamide (10 mL of a 1.5M solution in cyclohexane) and tetrahydrofuran (40 mL) under an argon atmosphere and cool to 0° C. Add, by dropwise addition, phenylacetylene (1.65 mL, 15 mmol). Remove the cooling bath and stir for 30 minutes as room temperature. Cool the yellow solution to 0° C. and add, by dropwise addition, N-methoxy-N-methylbenzamide (3.04 mL, 20 mmol). Remove the cooling bath and stir for 30 minutes at room temperature. Pour onto ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Purify by silica gel chromatography (2% ethyl acetate/hexane) then purify further by distillation (2×) to yield 1.9 g of the title compound; bp 210° C. in vacuo.

後処理

  1. customRemove the cooling bath
  2. temperatureCool the yellow solution to 0° C.
  3. customRemove the cooling bath
  4. stirringstir for 30 minutes at room temperature
  5. additionPour onto ethyl ether and water
  6. customseparate the organic phase
  7. dry with materialdry (MgSO4)
  8. filtrationFilter
  9. customevaporate the solvent in vacuo
  10. customto yield an oil
  11. customPurify by silica gel chromatography (2% ethyl acetate/hexane)
  12. distillationthen purify further by distillation (2×)

出典と根拠

ORDレコード
ord-2aabad6285ab40aaa1f0ffe29c00c7a8
出典データセット
uspto-grants-1993_09
特許番号
US05248825

関連ノート

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