Allyl bromide → HCID 13732612, compound

HRID 330382Notes

Reaction equation

HRID 330382 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].C(O[C:9](=[O:26])[CH2:10][CH:11]([OH:25])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])C.[CH2:27](Br)[CH:28]=[CH2:29].[Cl-].[NH4+]>C1COCC1>[CH2:1]([C:9]([OH:26])([CH2:10][CH:11]([OH:25])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:29][CH:28]=[CH2:27])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 13732611HCID 13732611, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 13732612HCID 13732612, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a small amount of freshly prepared allyl magnesium bromide and 1.7 g of Mg (0.07 mole) covered with THF was added a solution of 3.7 g of 3-hydroxyhexadecanoic acid ethyl ester (0.0123 mole) and 6.05 g (0.05 mole) of allyl bromide in 100 ml of THF. The addition proceeded so as to maintain a reflux temperature. The mixture was heated at refluxing temperature for 1 hr., cooled, and poured into saturated aq. ammonium chloride solution. The mixture was extracted with ether and the ether solution was dried over MgSO4 and distilled to dryness. The crude product weighed 5.0 g and could be used without further purification. The product could be purified by column chromatography on silica gel using ethyl acetate-hexane (15:85) as the eluant; δ (CDCl3), 1.28(CH2), 4.90-5.25(m, =CH2) and 5.4-6.2(m,=CH).

Workup

  1. additionThe addition
  2. temperatureto maintain a reflux temperature
  3. temperatureThe mixture was heated
  4. temperatureat refluxing temperature for 1 hr
  5. temperature, cooled
  6. extractionThe mixture was extracted with ether
  7. dry with materialthe ether solution was dried over MgSO4
  8. distillationdistilled to dryness
  9. customcould be used without further purification
  10. customThe product could be purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-52bc9a3728fc48e6ad7c323e58c21408
Source dataset
uspto-grants-1990_01
Patent number
US04895973

Reaction notes

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