Dimethylformamide → 5-Methoxybenzo[d][1,3]dioxole-4-carbaldehyde

HRID 594288ノート

反応式

HRID 594288 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.CN(C)CCN(C)C.[Li]CCCC.CN([CH:28]=[O:29])C.[NH4+].[Cl-]>C1COCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[C:4]=1[CH:28]=[O:29]

参加物

8

反応物 5

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 5924531,3-Benzodioxole, 5-methoxy-HCID 178418339Butyllithium

生成物 1

HCID 109760805-Methoxybenzo[d][1,3]dioxole-4-carbaldehyde

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

A cooled (−20° C.) mixture of 5-methoxybenzo[d][1,3]dioxole (4.560 g; 30.00 mmol), and N1,N1,N2,N2-tetramethylethane-1,2-diamine (5.36 ml; 36.00 mmol) in anh. THF (300 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (18.75 ml; 30.00 mmol). The resulting mixture was further stirred at −20° C. for 1 h. Anh. DMF (12.0 ml; 154.98 mmol) was then added, and the mixture was stirred at rt for 20 min. Aq. sat. NH4Cl and Et2O were successively added, and the aq. layer was further extracted with Et2O. The mixed organic layers were washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=1/1) afforded 5-methoxybenzo[d][1,3]dioxole-4-carbaldehyde as a yellow oil. LC-MS (conditions A): tR=0.55 min.; [M+H]+: 181.09 g/mol.

後処理

  1. temperatureA cooled
  2. stirringthe mixture was stirred at rt for 20 min
  3. extractionthe aq. layer was further extracted with Et2O
  4. washThe mixed organic layers were washed with water
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (heptane/AcOEt=1/1)

出典と根拠

ORDレコード
ord-31df38b4c87a47a7b2b4e0ad6c3c87a4
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

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