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

HRID 484471
ノート
印刷プレビュー

反応式

HRID 484471 の反応式
[OH-].[Na+].C([O-])(=O)C.[Pb+2].C([O-])(=O)C.F[B-](F)(F)F.[CH3:17][C:18]([C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([C:28]([CH3:31])([CH3:30])[CH3:29])[Se+:22]=1)([CH3:20])[CH3:19].[Cl:32][C:33]1[C:34](=[O:40])[C:35]([Cl:39])([Cl:38])[C:36]=1Cl>ClCCl.C(N(CC)CC)C>[CH3:20][C:18]([C:21]1[Se:22][C:23]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][C:25](=[CH:27][C:36]2[C:35]([Cl:39])([Cl:38])[C:34](=[O:40])[C:33]=2[Cl:32])[CH:26]=1)([CH3:17])[CH3:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 9317Lead diacetateHCID 14798Sodium HydroxideHCID 185452,3,4,4-Tetrachloro-2-cyclobuten-1-oneHCID 120389182,6-Bis(1,1-dimethylethyl)-4-methylselenopyrylium tetrafluoroborate

生成物 1

HCID 120389193-[[2,6-bis(1,1-dimethylethyl)-4H-selenopyran-4-ylidene]methyl]-2,4,4-trichlorocyclobut-2-en-1-one収率 60%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒2 回

実験手順

A 500 mL three-necked round-bottom flask was equipped with a magnetic stirrer, a dropping funnel with a pressure-equalizing side arm, a condenser with a dry nitrogen gas inlet tube and an outlet attached to a succession of scrubbers containing 10% aqueous sodium hydroxide and 10% aqueous lead acetate. Into this flask were placed 2,6-bis(1,1-dimethylethyl)-4-methyl-selenopyrylium tetrafluoroborate (3.0 g, 8.4 mmole, prepared as in Example 4 above, 2,3,4,4-tetrachlorocyclobut-2-en-1-one (1.7 g, 8.4 mmole) and dichloromethane (150 mL). Stirring was begun and a solution of triethylamine (2.3 mL, 16 mmole) in dichloromethane (50 mL) was added dropwise over a period of 1.5 hours under nitrogen. After the addition of the triethylamine had been completed, the reaction mixture was stirred at room temperature for an additional 1.5 hours, then filtered through a sintered glass funnel containing silica gel (40 g). The silica gel was washed several times with small portions of dichloromethane until the washings were pale orange. The filtrate and washings were combined and evaporated to dryness on a rotary evaporator on a water bath kept at approximately 40° C. The residual green mass was triturated with hexane (60 mL) until maroon crystals formed; these crystals were removed by suction filtration and dried in vacuo at approximately 30° C. to yield 3-[2,6-bis(1,1-dimethylethyl)-(4H-selenopyran-4-ylidene)methyl]-2,4,4-trichloro-cyclobut-2-en-1-one (2.2 g, 60% yield).

後処理

  1. customA 500 mL three-necked round-bottom flask was equipped with a magnetic stirrer, a dropping funnel with a pressure-equalizing side arm, a condenser with a dry nitrogen gas inlet tube and an outlet
  2. customInto this flask were placed
  3. stirringthe reaction mixture was stirred at room temperature for an additional 1.5 hours
  4. filtrationfiltered through a sintered glass funnel
  5. additioncontaining silica gel (40 g)
  6. washThe silica gel was washed several times with small portions of dichloromethane until the washings
  7. customevaporated to dryness on a rotary evaporator on a water bath
  8. customkept at approximately 40° C
  9. customThe residual green mass was triturated with hexane (60 mL) until maroon crystals
  10. customformed
  11. customthese crystals were removed by suction filtration
  12. customdried in vacuo at approximately 30° C.

出典と根拠

ORDレコード
ord-2185afb54b8a419ebc331212ed56eacb
出典データセット
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05231190

反応ノート

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