Tributyltin Chloride → HCID 15288193, 화합물

HRID 362371노트

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HRID 362371 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

HCID 15288193HCID 15288193, 화합물

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dd239aaa3f594480b247f768f22cde37
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05869483

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