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

HRID 280394

Reaction equation

HRID 280394 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1d627643a6b3400ab96df2d3cc7f0861
Source dataset
uspto-grants-1986_05
Patent number
US04588828

Linked notes

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