Allyl bromide → HCID 22730363、化合物

HRID 2356075ノート

反応式

HRID 2356075 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.[Li+].[CH3:13][CH:14]([N-]C(C)C)[CH3:15].C1CCCCC1.C(Br)C=C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][CH2:15][CH:14]=[CH2:13])=[N:7][C:6]=2[CH:11]=1

参加物

6

反応物 4

HCID 7841Allyl bromideHCID 8078CyclohexaneHCID 2724682Lithium diisopropylamideHCID 30174575-Bromo-2-methylbenzothiazole

生成物 1

HCID 22730363HCID 22730363、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-bromo-2-methylbenzothiazole (1.00 g, 4.38 mmol) in THF (25 mL) at −78° C. was treated with 1.5M LDA in cyclohexane (4.40 mL, 6.60 mmol), stirred for 45 minutes, treated with allyl bromide (1.33 g, 10.99 mmol), stirred for 1 hour, quenched with 1M HCl, warmed to room temperature, added to water (50 mL), and extracted with ethyl acetate (3×200 mL). The combined extracts were washed with brine (25 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 8% ethyl acetate/hexanes to provide the desired product.

後処理

  1. stirringstirred for 1 hour
  2. customquenched with 1M HCl
  3. additionadded to water (50 mL)
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. washThe combined extracts were washed with brine (25 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash column chromatography on silica gel with 8% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-c8290b8a4b0344a4879955ffc9e88895
出典データセット
uspto-grants-2010_07
特許番号
US07754886B2

反応ノート

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