Nitrogen → Benzaldehyde, 3-(2-methyl-1,3-dioxolan-2-yl)-

HRID 42758ノート

反応式

HRID 42758 の反応式
N#N.Br[C:4]1[CH:5]=[C:6]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[CH:7]=[CH:8][CH:9]=1.[Li]CCCC.CN([CH:24]=[O:25])C.[NH4+].[Cl-]>C1COCC1.CCCCCC>[CH3:15][C:10]1([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[CH:24]=[O:25])[O:14][CH2:13][CH2:12][O:11]1

参加物

8

反応物 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 109992182-(3-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 178418339Butyllithium

生成物 1

HCID 10607757Benzaldehyde, 3-(2-methyl-1,3-dioxolan-2-yl)-

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-(3-bromo-phenyl)-2-methyl-[1,3]dioxolane (944 mg, 3.88 mmol) in THF (20.0 mL) at −78° C. was added dropwise n-BuLi (1.60 mL of a 2.5M solution in hexane, 4.00 mmol). The reaction mixture was then stirred for 30 min at −78° C. before DMF (0.40 mL, 5.17 mmol) was added dropwise. The reaction mixture was allowed to warm to rt over 1 h. Sat. aq. NH4Cl was added and the mixture was extracted three times with Et2O. The combined org. extracts were dried over NaSO4, filtered, and the solvent was removed under reduced pressure to give the crude title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.87 min.

後処理

  1. additionwas added dropwise
  2. extractionthe mixture was extracted three times with Et2O
  3. dry with materialextracts were dried over NaSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-90a55e5f33de4baa848ce405b9ff3ca6
出典データセット
uspto-grants-2013_09
特許番号
US08536209B2

反応ノート

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