Diisopropyl Ether → 1(RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-prop-2-ynyl alcohol

HRID 231841

반응식

HRID 231841 반응식
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:14])=[C:5]1[C:15]([F:18])([F:17])[F:16])[C:2]#[CH:3].[C:19](Br)#[CH:20].[Mg].[Mg].P(O)(O)([O-])=O.[Na+].C(OC(C)C)(C)C>O1CCCC1>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([OH:14])[C:19]#[CH:20])=[C:5]1[C:15]([F:18])([F:16])[F:17])[C:2]#[CH:3]

참가 물질

7

반응물 5

HCID 7914Diisopropyl EtherHCID 5462224MagnesiumHCID 200321241-(2-propynyl)-2-trifluoromethyl-3-formyl-(1H)-indolHCID 23672064Monosodium phosphateHCID 87069377Magnesium ethynyl bromide

생성물 1

HCID 886197831(RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-prop-2-ynyl alcohol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-5 °C

실험 절차

4.5 g of 1-(2-propynyl)-2-trifluoromethyl-3-formyl-(1H)-indole in 30 ml of tetrahydrofuran were cooled at -15° C. and over 15 minutes, 26 ml of a solution of magnesium ethynyl bromide in tetrahydrofuran (0.8M ) were added. After stirring for one hour at -5° C., another 5 ml of magnesium solution were added, and the mixture was allowed to return to ambient temperature. After stirring for 30 minutes and then pouring into a saturated aqueous solution of monosodium phosphate, extraction was carried out with isopropyl ether. The solvent was eliminated under reduced pressure to obtain 5.89 g of crude product which was purified by chromatography over silica (eluent: hexane-ethyl acetate 9-1) to obtain 1.91 g of 1(RS) [1-(2-propynyl)-2-trifluoromethyl-(1H)-indol-3-yl]-prop-2-ynyl alcohol melting at 98° C.

후처리

  1. customto return to ambient temperature
  2. stirringAfter stirring for 30 minutes
  3. customto obtain 5.89 g of crude product which
  4. customwas purified by chromatography over silica (eluent: hexane-ethyl acetate 9-1)

출처 및 근거

ORD 기록
ord-05a2817af28a4a6bbaab96a48c6c9130
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04849443

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