Dichlorodimethylsilane → Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane

HRID 1037712

反応式

HRID 1037712 の反応式
[CH3:1][CH:2]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[CH:4]=[C:3]1[CH3:10].CC1C2C=CSC=2CC=1C.[Li]CCCC.[Cl:26][Si:27](Cl)([CH3:29])[CH3:28]>C1COCC1>[Cl:26][Si:27]([CH:4]1[C:5]2[S:6][CH:7]=[CH:8][C:9]=2[C:2]([CH3:1])=[C:3]1[CH3:10])([CH3:29])[CH3:28]

参加物

6

反応物 4

HCID 6398DichlorodimethylsilaneHCID 123075884,5-dimethyl-4H-cyclopenta[b]thiopheneHCID 668093064,5-dimethyl-6H-cyclopenta[b]thiopheneHCID 178418339Butyllithium

生成物 1

HCID 58526148Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under an argon atmosphere, to a solution of 10.0 g (66.6 mmol) of a mixture of 4,5-dimethyl-4H-cyclopenta[b]thiophene and 4,5-dimethyl-6H-cyclopenta[b]thiophene in 150 ml of THF, 26.6 ml of 2.5 M (66.6 mmol) nBuLi in hexanes was added dropwise over 30 minutes at −60° C. This mixture was additionally stirred for 2 hours at room temperature and then added dropwise for 3 hours to a solution of 23.7 ml (25.2 g, 200 mmol) of dichlorodimethylsilane in 50 ml of THF. The resulting mixture was stirred for 12 hours at ambient temperature and then evaporated to dryness. Fractional distillation gave yellowish liquid, bp 83-85° C./0.2 mm Hg. Yield 10.7 g (66%).

後処理

  1. stirringThe resulting mixture was stirred for 12 hours at ambient temperature
  2. customevaporated to dryness
  3. distillationFractional distillation
  4. customgave yellowish liquid, bp 83-85° C./0.2 mm Hg

出典と根拠

ORDレコード
ord-77d263a97fae40958d9657850a6788c1
出典データセット
uspto-grants-2013_10
特許番号
US08546595B2

関連ノート

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