Trimethyltin chloride → 2-(Benzo[d]oxazol-2-yl)benzaldehyde

HRID 1422145노트

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HRID 1422145 반응식
C([Sn](CCCC)(CCCC)[C:6]1[O:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1)CCC.C([Sn](Cl)(CCCC)CCCC)CCC.C[Sn](Cl)(C)C.Br[C:43]1[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=1[CH:45]=[O:46]>C1(C)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>[O:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=[C:6]1[C:43]1[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=1[CH:45]=[O:46]

참가 물질

7

반응물 4

HCID 14016Trimethyltin chlorideHCID 15096Tributyltin ChlorideHCID 811292-BromobenzaldehydeHCID 37665862-(Tributylstannyl)-1,3-benzoxazole

생성물 1

HCID 183576892-(Benzo[d]oxazol-2-yl)benzaldehyde수율 84.9%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 7237O-Xylene용매

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온도
115 °C

실험 절차

A mixture of 12.5 g of 2-tributylstannylbenzoxazole (prepared by the method of P. Jutzi and W. Gilge, J. Organometallic Chem. 1983, 246, 159, using tributyltin chloride as a less toxic replacement for trimethyltin chloride) 5.66 g 2-bromobenzaldehyde, and 0.46 g tetrakis(triphenylphosphine)-palladium (0) in 300 ml of anhydrous xylene under a nitrogen atmosphere was heated to 115° C. for 12 h. The reaction mixture was cooled to room temperature and evaporated to dryness under reduced pressure. The resulting oil was purified by chromatography on silica eluting with ethyl acetate-heptane (1:5) to afford 5.8 g of 2-(benzoxazol-2-yl)benzaldehyde, GC-M.S. (E.I.) (M/Z): 223 [M+ ].

후처리

  1. customprepared by the method of P
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customevaporated to dryness under reduced pressure
  4. customThe resulting oil was purified by chromatography on silica eluting with ethyl acetate-heptane (1:5)

출처 및 근거

ORD 기록
ord-983363f6fcd943e9aa17f0ace0e5a2f2
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06080773

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