Dimethylformamide → 2,3-Dihydrobenzofuran-6-carbaldehyde

HRID 2264152노트

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HRID 2264152 반응식
Br[C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.C([Li])CCC.CN([CH:19]=[O:20])C>C1COCC1.CCCCCC>[O:8]1[C:4]2[CH:3]=[C:2]([CH:19]=[O:20])[CH:10]=[CH:9][C:5]=2[CH2:6][CH2:7]1

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 112526166-Bromo-2,3-dihydro-1-benzofuranHCID 178418339Butyllithium

생성물 1

HCID 149643942,3-Dihydrobenzofuran-6-carbaldehyde

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

To an cooled solution (−78° C. internal temp) of 1 g of 6-bromo-2,3-dihydro-1-benzofuran (prepared as described by Z. J. Song, M. Zhao, L. Frey, J. Li, L. Tan, C. Y. Chen, D. M. Tschaen, R. Tillyer, E. J. J. Grabowski, R. Volante, P. J. Reider, Y. Kato, S. Okada, T. Nemoto, H. Sato, A. Akao, T. Mase, Organic Letters, 2001, Vol. 3, No. 21, 3357-3360) in 20 mL of anhydrous THF was added 4 mL of 2.5 M n-butyllithium in hexane. After stirring 10 min at −78° C., 0.5 mL of anhydrous DMF was added and the mixture allowed to warm to −20° C., quenched with 20 mL of 3N HCl and extracted into 2×50 mL of ether. Combined extracts dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (0-20% ethyl acetate in hexanes) gave the product as white crystalline solid. MS (m+1)=149.1; 1H NMR (400 MHz, CDCl3) 9.9 (s, 1H), 7.4 (m, 2H), 7.3 (s, 1H), 4.62 (t, 2H), 3.28 (t, 4H).

후처리

  1. temperatureto warm to −20° C.
  2. customquenched with 20 mL of 3N HCl
  3. extractionextracted into 2×50 mL of ether
  4. dry with materialCombined extracts dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (0-20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-843e3c2b701949c494ffab7051276bc8
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855201B2

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