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

HRID 42758노트

반응식

HRID 42758 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-90a55e5f33de4baa848ce405b9ff3ca6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

반응 노트

불러오는 중…