Dibutyl Vinylboronate (stabilized with Phenothiazine) → 4-Vinylfuran-2-carbaldehyde

HRID 1363283

반응식

HRID 1363283 반응식
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=1.[CH2:9](OB(C=C)OCCCC)[CH2:10]CC.ClC1C=CC(CC2C=C(C=O)SC=2)=CC=1>CN(C=O)C>[CH:9]([C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[O:5][CH:6]=1)=[CH2:10]

참가 물질

5

반응물 3

HCID 236543Dibutyl Vinylboronate (stabilized with Phenothiazine)HCID 27570104-Bromo-2-furaldehydeHCID 596485254-(4-Chlorobenzyl)thiophene-2-carbaldehyde

생성물 1

HCID 596485494-Vinylfuran-2-carbaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The title compound was synthesized from 4-bromo-furan-2-carbaldehyde (1.1 g, 6.29 mmol) and vinylboronic acid dibutyl ester (1.67 mL, 7.54 mmol) using the same conditions used to synthesize 4-(4-chlorobenzyl)thiophene-2-carbaldehyde, with the exception that the reaction was run in DMF (20 mL). Purification by flash chromatography (0-30% EtOAc in heptane) provided 4-vinylfuran-2-carbaldehyde as an orange oil; Yield 282 mg (37%). 1H NMR (400 MHz, CDCl3) δ ppm 5.31 (dd, J=10.88, 0.93 Hz, 1H), 5.61 (dd, J=17.57, 0.54 Hz, 1H), 6.56 (dd, J=17.55, 10.91 Hz, 1H), 7.37 (s, 1H), 7.67 (s, 1H), 9.66 (d, J=0.59 Hz, 1H).

후처리

  1. customPurification by flash chromatography (0-30% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-d36860b2be314c0289845e998888835e
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884124B2

연결된 노트

불러오는 중…