Tributyltin Chloride → HCID 15288193、化合物

HRID 362371ノート

反応式

HRID 362371 の反応式
[CH3:1][C:2]1([CH3:12])[CH2:6][O:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:3]1.C([Li])CCC.C([Sn](Cl)(CCCC)CCCC)CCC.CC1(C)COC(C2SC=CC=2[Sn](CCCC)(CCCC)CCCC)=N1.[N+:57]([C:60]1[CH:67]=[CH:66][CH:65]=[CH:64][C:61]=1[CH2:62]Br)([O-:59])=[O:58]>CCOCC.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[CH2:6][O:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[CH2:62][C:61]2[CH:64]=[CH:65][CH:66]=[CH:67][C:60]=2[N+:57]([O-:59])=[O:58])=[N:3]1

参加物

9

反応物 5

HCID 15096Tributyltin ChlorideHCID 77569alpha-Bromo-2-nitrotolueneHCID 50082824,5-dihydro-4,4-dimethyl-2-(2-thienyl)-oxazoleHCID 15288192HCID 15288192、化合物HCID 178418339Butyllithium

生成物 1

HCID 15288193HCID 15288193、化合物

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 4,5-dihydro-4,4-dimethyl-2-(2-thienyl)-oxazole (4.5 gms 25 mmol) in anhydrous ether at -70° C., n-butyl-lithium (2.5 molar solution in hexane, 11 ml) is added drop by drop under N2 atmosphere. The reaction mixture is stirred at -78° C. for 45 minutes and tri-n-butyltin chloride (8.3 gms 25 mmol) in dry ether is added drop by drop. The reaction mixture is stirred at room temperature for 1 hour and quenched with water. The reaction mixture is extracted with ether, washed well with water, dried and concentrated. The product obtain is pure enough for further transformation. The oil product, 4,5-dihydro-4,4-dimethyl-2-[3-(tributylstannyl)-2-thienyl]-oxazole is mixed with 2-nitrobenzyl bromide (5.5 g 25 mmol) in toluene and refluxed in the presence of tetrakis (triphenylphosphine)-palladium (0) (200 mg) for 16 hours.

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 1 hour
  2. customquenched with water
  3. extractionThe reaction mixture is extracted with ether
  4. washwashed well with water
  5. customdried
  6. concentrationconcentrated
  7. customThe product obtain

出典と根拠

ORDレコード
ord-dd239aaa3f594480b247f768f22cde37
出典データセット
uspto-grants-1999_02
特許番号
US05869483

反応ノート

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