Diethyl Ether → HCID 21501105, compound

HRID 1729780Notes

Reaction equation

HRID 1729780 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].CCOCC.[Cl-].[NH4+]>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 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 21501148HCID 21501148, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 21501105HCID 21501105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.5 G. of 6-[4-tertiarybutoxypentyl]-2-tetrahydropyranol produced in Example 120 was dissolved in 200 ml. of tetrahydrofuran and added slowly over a 20 minute period to a solution of 300 ml. of vinyl magnesium chloride in tetrahydrofuran at 0°. After agitation for an additional hour at room temperature, 200 ml. of ether was added which was followed by the addition of 100 ml. of a 20 per cent aqueous solution of ammonium chloride. Extraction with ether yielded a waxy solid, 3,7-dihydroxy-11-tertiarybutoxydodec-1-ene.

Workup

  1. customat 0°
  2. waitAfter agitation for an additional hour at room temperature
  3. additionwas followed by the addition of 100 ml
  4. extractionExtraction with ether

Sources & evidence

ORD record
ord-29be0a1c95de4716bed010896b892179
Source dataset
uspto-grants-1976_11
Patent number
US03989724

Reaction notes

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