Triethylamine → 3-[[2,6-bis(1,1-dimethylethyl)-4H-selenopyran-4-ylidene]methyl]-2,4,4-trichlorocyclobut-2-en-1-one

HRID 484472

반응식

HRID 484472 반응식
C(N(CC)CC)C.F[B-](F)(F)F.[CH3:13][C:14]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[Se+:18]=1)([CH3:16])[CH3:15].[Cl:28][C:29]1[C:30](=[O:36])[C:31]([Cl:35])([Cl:34])[C:32]=1Cl.[OH-].[Na+]>ClCCl>[CH3:16][C:14]([C:17]1[Se:18][C:19]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][C:21](=[CH:23][C:32]2[C:31]([Cl:35])([Cl:34])[C:30](=[O:36])[C:29]=2[Cl:28])[CH:22]=1)([CH3:13])[CH3:15]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 185452,3,4,4-Tetrachloro-2-cyclobuten-1-oneHCID 120389182,6-Bis(1,1-dimethylethyl)-4-methylselenopyrylium tetrafluoroborate

생성물 1

HCID 120389193-[[2,6-bis(1,1-dimethylethyl)-4H-selenopyran-4-ylidene]methyl]-2,4,4-trichlorocyclobut-2-en-1-one수율 71.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of triethylamine (14.8 g, 147 mmol) in dichloromethane (40 mL) was added dropwise under nitrogen to a solution of 2,6-bis(1,1-dimethylethyl)-4-methylselenopyrylium tetrafluoroborate (26.2 g, 73.4 mmol, prepared in Examples 4 and 5 above) and 2,3,4,4-tetrachlorocyclobut-2-en-1-one (15.2 g, 73.4 mmol) in dichloromethane (60 mL), contained in a flask equipped with a condenser and an outlet connected to a gas-washing bottle containing 10% aqueous sodium hydroxide solution; the addition was effected at a rate such that the temperature of the reaction mixture did not exceed 35° C. After the addition had been completed, the reaction mixture was stirred for one hour, then applied to a column packed with silica gel. Elution with dichloromethane, followed by evaporation of the solvent under reduced pressure, provided the crude product which was further purified by trituration with trifluoroethanol for one hour to give 3-[[2,6-bis(1,1,-dimethylethyl)-4H-selenopyran-4-ylidene]methyl]-2,4,4-trichlorocyclobut-2-en-1-one (23 g, 71% yield) as maroon crystals. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

후처리

  1. customcontained in a flask
  2. customequipped with a condenser and an outlet
  3. additionthe addition
  4. customdid not exceed 35° C
  5. additionAfter the addition
  6. washElution with dichloromethane
  7. customfollowed by evaporation of the solvent under reduced pressure
  8. customprovided the crude product which
  9. customwas further purified by trituration with trifluoroethanol for one hour

출처 및 근거

ORD 기록
ord-f35a6d18a5f44a41a5981bb95fc6dc03
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05231190

연결된 노트

불러오는 중…