Water → 3,3-Dimethyl-2,3-dihydro-1-benzofuran

HRID 460304ノート

反応式

HRID 460304 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.C([Li])CCC.CCCCCC.O>O1CCCC1>[CH3:10][C:7]1([CH3:11])[C:6]2[CH:12]=[CH:2][CH:3]=[CH:4][C:5]=2[O:9][CH2:8]1

参加物

6

反応物 4

HCID 962WaterHCID 8058HexaneHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuranHCID 178418339Butyllithium

生成物 1

HCID 111593943,3-Dimethyl-2,3-dihydro-1-benzofuran収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (example 1f) (3.3 g, 14.53 mmol) in tetrahydrofuran (30 mL) was added dropwise, at −78° C., under an atmosphere of argon, a solution of n-butyllithium in hexane (8.8 mL, 22 mmol). The mixture was stirred at −78° C. for 5 minutes, then water was added and the mixture was warmed up to room temperature and stirred for 30 minutes. The layers were separated. The aqueous layer was extracted twice with ethyl acetate and the organic combined extract was washed with water, brine, dried (MgSO4), and filtered. The solvent was evaporated to afford 2.13 g of 3,3-dimethyl-2,3-dihydro-benzofuran. 99% yield. 1H-NMR (300 MHz, CDCl3): 1.35 (s, 6H), 4.23 (s, 2H), 6.79 (d, J=7.6 Hz, 1H), 6.88 (t, J=7.3 Hz, 1H), 7.11 (d, J=7.6 Hz, 2H).

後処理

  1. temperaturethe mixture was warmed up to room temperature
  2. stirringstirred for 30 minutes
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. extractionthe organic combined extract
  6. washwas washed with water, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-e62fb9551e244d029c84549865eab78c
出典データセット
uspto-grants-2007_03
特許番号
US07196108B2

反応ノート

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