Allyl bromide → 8-(1-(Allyloxy)allyl)-1,4-dioxaspiro[4.5]decane

HRID 2175496Notes

Reaction equation

HRID 2175496 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([OH:14])[CH:12]=[CH2:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19]>>[CH2:19]([O:14][CH:11]([CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[CH:12]=[CH2:13])[CH:18]=[CH2:17]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 585627571-(1,4-Dioxaspiro[4.5]decan-8-yl)prop-2-en-1-ol

Product 1

HCID 585627078-(1-(Allyloxy)allyl)-1,4-dioxaspiro[4.5]decane

Procedure

A solution of 1-(1,4-dioxaspiro[4.5]decan-8-yl)prop-2-en-1-ol (414 mg, 2.09 mmol), prepared in the previous step, was added to a suspension of sodium hydride (104 mg, 4.12 mmol, 95%) dropwise at 0° C. under argon. After the complete addition, the reaction mixture was allowed to reach room temperature and stirred for 1 hour. Allyl bromide (0.35 mL, 4.05 mmol) was added dropwise and the mixture stirred overnight at room temperature. It was poured onto ice cooled saturated NaHCO3 solution. After extraction with ether, the organic layer was concentrated in vacuo and the residue purified by flash chromatography (silica gel, DCM) to afford the product.

Workup

  1. additionAfter the complete addition
  2. customto reach room temperature
  3. stirringthe mixture stirred overnight at room temperature
  4. additionIt was poured onto ice cooled saturated NaHCO3 solution
  5. extractionAfter extraction with ether
  6. concentrationthe organic layer was concentrated in vacuo
  7. customthe residue purified by flash chromatography (silica gel, DCM)
  8. customto afford the product

Sources & evidence

ORD record
ord-1c071aff3bdc431ca5121770a16ee9d7
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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