Dimethylformamide → 2,3-Dihydrobenzofuran-6-carbaldehyde

HRID 2264152ノート

反応式

HRID 2264152 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 149643942,3-Dihydrobenzofuran-6-carbaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-843e3c2b701949c494ffab7051276bc8
出典データセット
uspto-grants-2010_12
特許番号
US07855201B2

反応ノート

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