Dimethylformamide → 5-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde

HRID 1989818ノート

反応式

HRID 1989818 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[CH2:10])[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1>[CH3:11][C:8]([C:6]1[CH:5]=[CH:4][C:3]([O:13][CH3:14])=[C:2]([CH:7]=1)[CH:23]=[O:24])([CH3:12])[CH:9]=[CH2:10]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 112422612-Bromo-4-(1,1-dimethyl-allyl)-1-methoxy-benzeneHCID 178418339Butyllithium

生成物 1

HCID 113331815-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of 2-Bromo-4-(1,1-dimethyl-allyl)-1-methoxy-benzene (3.1 g, 0.012 mol) in dry THF (50 mL) was cooled to −78° C. under argon. n-BuLi (2.5M, 5.1 mL, 0.0128 mol) was added keeping the temperature below −70° C. The yellow mixture was stirred for another 15 min and quenched with dry DMF (1.4 mL, 0.018 mol). The cooling bath was removed and the mixture was allowed to warm to 25° C. A saturated solution of NaHCO3 (30 mL) was added and then extracted with EtOAc (3×50 mL). The organic phase was dried (Na2SO4) and evaporated to yellow oil. Yield: 2.31 g (94%).

後処理

  1. customthe temperature below −70° C
  2. customThe cooling bath was removed
  3. additionA saturated solution of NaHCO3 (30 mL) was added
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated to yellow oil

出典と根拠

ORDレコード
ord-ada405e7b3eb4dd8838b9f85449f6475
出典データセット
uspto-grants-2010_01
特許番号
US07642367B2

反応ノート

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