Dimethylformamide → 2,2-Dimethylbenzo[d][1,3]dioxole-5-carbaldehyde

HRID 855335

反応式

HRID 855335 の反応式
C1([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)CC1.BrC1C=CC2[O:17][C:18]([CH3:21])([CH3:20])[O:19]C=2C=1.[Li]CCCC.CCCCCC.CN(C=O)C>>[CH3:20][C:18]1([CH3:21])[O:19][C:4]2[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][C:11]=2[O:17]1

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 8058HexaneHCID 115064744-CyclopropylbenzaldehydeHCID 115938035-Bromo-2,2-dimethylbenzo(d)(1,3)dioxoleHCID 178418339Butyllithium

生成物 1

HCID 5960122,2-Dimethylbenzo[d][1,3]dioxole-5-carbaldehyde収率 83%

実験手順

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 420 mg of 5-bromo-2,2-dimethyl-benzo[1,3]dioxole [CAS 73790-19-9] (1.83 mmol), 1.38 ml of a 1.6 molar solution of n-BuLi in hexane (2.20 mmol) and 712 μl of DMF (9.17 mmol). The isolated residue was purified by flash column chromatography (1:9 ether/pentane) to give 270 mg of 2,2-dimethyl-benzo[1,3]dioxole-5-carbaldehyde (83%) as a light yellow liquid. 1H NMR (CDCl3, 300 MHz): δ 1.72 (s, 6H), 6.84 (d, J=7.8 Hz, 1H), 7.26 (s, 1H), 7.87 (dd, J=8.0 and 1.7 Hz, 1H), 9.97 (s, 1H).

後処理

  1. customThe isolated residue was purified by flash column chromatography (1:9 ether/pentane)

出典と根拠

ORDレコード
ord-133379b692704aecb11964eb767736a5
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

関連ノート

読み込み中…