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Dimethylformamide → 5-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxybenzaldehyde

HRID 1170994
ノート
印刷プレビュー

反応式

HRID 1170994 の反応式
[CH3:1][C:2]1[CH:18]=[C:17]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:16]=[C:15]([CH3:30])[C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[CH:7][CH:6]=1.CN(CCN(C)C)C.[Li]CCCC.CN([CH:47]=[O:48])C>CCOCC>[CH3:30][C:15]1[CH:16]=[C:17]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:21]([CH3:23])[CH3:22])[CH:24]([CH3:26])[CH3:25])[CH:18]=[C:2]([CH3:1])[C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[C:7]([CH:6]=1)[CH:47]=[O:48]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 666426914-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-methoxymethoxybenzeneHCID 178418339Butyllithium

生成物 1

HCID 866034575-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxybenzaldehyde収率 98.7%

試薬・触媒・溶媒 1

HCID 3283
Diethyl Ether
溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-methoxymethoxybenzene (2.0 g, 4.66 mmol) in ether was added TMEDA (1.05 mL, 6.99 mmol), followed by nBuLi (2.5 M in THF, 2.8 mL) at −20° C. The reaction mixture was warmed up to 0° C. and stirred for 1 h DMF (0.72 mL, 9.32 mmol) was then added and after stirring at 0° C. for 2 h, the reaction mixture was quenched with a saturated solution of NH4Cl and diluted with EtOAc. The water layer was extracted with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated to give the crude product 5-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxy-benzaldehyde (2.1 g, 98%): 1H NMR (300 MHz, d6-DMSO): δ 10.33 (s, 1H), 7.24 (m, 3H), 6.58 (s, 2H), 5.31 (s, 2H), 3.91 (s, 2H), 3.33 (s, 6H), 1.23 (m, 3H), 1.06 (m, 18H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.55.

後処理

  1. additionwas then added
  2. customthe reaction mixture was quenched with a saturated solution of NH4Cl
  3. additiondiluted with EtOAc
  4. extractionThe water layer was extracted with EtOAc
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-a0672c0d47e1436492d4c4e01169bc1f
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07829552B2

反応ノート

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