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

HRID 6491

반응식

HRID 6491 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 976371,3-Diphenyl-2-propyn-1-one수율 61.4%

시약·촉매·용매 1

HCID 8078Cyclohexane용매

실험 절차

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.

후처리

  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×)

출처 및 근거

ORD 기록
ord-2aabad6285ab40aaa1f0ffe29c00c7a8
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248825

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