Dimethyl Sulfide → (S)-4-formylbut-3-yn-2-yl acetate

HRID 1170402

반응식

HRID 1170402 반응식
[C:1]([O:4][C@H:5]([C:7]#[C:8]/[CH:9]=C/C1C=CC=CC=1)[CH3:6])(=[O:3])[CH3:2].[O:17]=[O+][O-].CSC>CO>[C:1]([O:4][C@H:5]([C:7]#[C:8][CH:9]=[O:17])[CH3:6])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 59552201(E)-(2S)-6-phenylhex-5-en-3-yn-2-yl acetate

생성물 1

HCID 11499231(S)-4-formylbut-3-yn-2-yl acetate수율 81%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
23 °C

실험 절차

A solution of 8 (392 mg, 1.83 mmol) in methanol (4.6 mL) was treated with O3 for 3 min at −78° C. After removing excess O3, the reaction was quenched by slow addition of methylsulfide (1.35 mL, 18.3 mmol) at −78° C. The resulting mixture was stirred for 1 h at −78° C. and for 1 h at 23° C., and then concentrated in vacuo. Purification of the residue via flash chromatography (silica gel 16 mL; 5→15% EtOAc in hexanes) afforded aldehyde 9 (208 mg, 81%) as a colorless oil.

후처리

  1. customAfter removing excess O3
  2. concentrationconcentrated in vacuo
  3. customPurification of the residue via flash chromatography (silica gel 16 mL; 5→15% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-f815ff3411f5476db58a4115b4ea6f15
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825267B2

연결된 노트

불러오는 중…