Tributylphosphine → (E)-3-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethoxy)-but-2-enoic acid ethyl ester

HRID 18992

반응식

HRID 18992 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][OH:12].[CH2:13]([O:15][C:16](=[O:20])[C:17]#[C:18][CH3:19])[CH3:14].C(P(CCCC)CCCC)CCC>O1CCCC1>[CH2:13]([O:15][C:16](=[O:20])/[CH:17]=[C:18](/[O:12][CH2:11][CH:2]1[O:1][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1)\[CH3:19])[CH3:14]

참가 물질

5

반응물 3

HCID 13831TributylphosphineHCID 193141,4-Benzodioxane-2-methanolHCID 78043Ethyl 2-butynoate

생성물 1

HCID 66899651(E)-3-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethoxy)-but-2-enoic acid ethyl ester수율 40.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred mixture of (2,3-dihydro-benzo[1,4]dioxin-2-yl)-methanol (1.01 g, 5.90 mmol) and ethyl-2-butynoate (820 mg, 7.08 mmol) in tetrahydrofuran (15 mL) was added tri-n-butylphosphine (0.25 g, 1.18 mmol). The mixture was stirred at room temperature for 1.5 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo. The crude product obtained was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 50% ethyl acetate/hexanes) to afford (E)-3-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethoxy)-but-2-enoic acid ethyl ester (660 mg, 40%) as a colorless oil: LR-ES-MS m/z calculated for C15H18O5 [M]+ 278, observed [M+H]+ 279.

후처리

  1. customwas removed in vacuo
  2. customThe crude product obtained
  3. customwas purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-424f5c5691384160a9ed055e17cf6b2b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

연결된 노트

불러오는 중…