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

HRID 280394

反応式

HRID 280394 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1d627643a6b3400ab96df2d3cc7f0861
出典データセット
uspto-grants-1986_05
特許番号
US04588828

関連ノート

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