Diethyl Ether → (trans)-3-(7-Phenyl-1,2-heptadiene-4,6-diynyl)oxiranemethanol

HRID 280394

반응식

HRID 280394 반응식
[CH2:1](O)/[CH:2]=[CH:3]/[CH2:4][OH:5].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1.O1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.CC[O:26]CC>>[C:7]1([C:17]#[C:19][C:20]#[C:21][CH:22]=[C:23]=[CH:1][C@@H:2]2[O:26][C@H:3]2[CH2:4][OH:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

5

반응물 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 175854trans-2-Butene-1,4-diol

생성물 1

HCID 86740795(trans)-3-(7-Phenyl-1,2-heptadiene-4,6-diynyl)oxiranemethanol

실험 절차

To a solution of trans-2-butene-1,4-diol (7.57 g, 85.9 mmole) and a catalytic quantity of p-toluenesulfonic acid in 700 ml of dry ether was added dihydropyran (6.73 ml, 71.6 mmole) at the rate of 1.5 ml/hour. After stirring for four days, the reaction mixture was washed with saturated sodium bicarbonate, and the organic layer was separated and dried over sodium sulfate and concentrated in vacuo to afford the crude product which was purified via flash chromatography (LPS-1 silica gel; ether-hexane 1:1) to provide the title compound (5.75 g).

후처리

  1. washthe reaction mixture was washed with saturated sodium bicarbonate
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product which
  6. customwas purified via flash chromatography (LPS-1 silica gel; ether-hexane 1:1)

출처 및 근거

ORD 기록
ord-1d627643a6b3400ab96df2d3cc7f0861
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588828

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