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

HRID 428040ノート

反応式

HRID 428040 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 7237O-Xylene溶媒

反応条件

温度
115 °C

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-a7e3dc93c7464dd4b7789e0929315555
出典データセット
uspto-grants-2001_11
特許番号
US06313139B1

反応ノート

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