Vinyl Chloride → HCID 21501105, compound

HRID 1729778Notes

Reaction equation

HRID 1729778 reaction equation
[C:1]([O:5][CH:6]([CH3:17])[CH2:7][CH2:8][CH2:9][CH:10]1[O:15][CH:14]([OH:16])[CH2:13][CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[CH:18]([Mg]Cl)=[CH2:19].[Mg].C(Cl)=C>O1CCCC1>[OH:16][CH:14]([CH2:13][CH2:12][CH2:11][CH:10]([OH:15])[CH2:9][CH2:8][CH2:7][CH:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:17])[CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 6338Vinyl ChlorideHCID 5462224MagnesiumHCID 21501148HCID 21501148, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 21501105HCID 21501105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 6-[4-(t-butoxy)pentyl]-tetrahydropyran-2-ol (5 g.) in tetrahydrofuran (50 ml.) was added within 30 minutes at 5° to a solution of vinyl magnesium chloride in tetrahydrofuran, prepared from magnesium (2.0 g.) and 4 g. of vinyl chloride, dissolved in tetrahydrofuran (50 ml.). After stirring overnight at room temperature, the reaction solution was treated with ammonium chloride-ice and then extracted with chloroform (3 times, each time 100 ml.). The organic phase was washed with water, dried and evaporated in vacuo giving crude 3,7-dihydroxy-11-(t-butoxy)-dodec-1-ene.

Workup

  1. extractionextracted with chloroform (3 times
  2. washThe organic phase was washed with water
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-e17621cbc7144e43826f644ecd5832e7
Source dataset
uspto-grants-1976_11
Patent number
US03989724

Reaction notes

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