Allyl bromide → HCID 57827423, compound

HRID 1693178Notes

Reaction equation

HRID 1693178 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:18])[CH2:11][CH:12]1[S:17][CH2:16][CH2:15][CH2:14][S:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23]>C1COCC1>[CH2:23]([O:18][C@@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:11][CH:12]1[S:17][CH2:16][CH2:15][CH2:14][S:13]1)[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 12102453HCID 12102453, compound

Product 1

HCID 57827423HCID 57827423, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-1-benzyloxy-3-[1,3]dithian-2-yl-propan-2-ol (22.1 g) in THF (300 mL) was cooled to 0° C. 60% sodium hydride (4.35 g) was added, followed by stirring. After 12 minutes, allyl bromide (10 mL) was added and then the ice bath was removed. The mixture was further stirred at room temperature. After stirring overnight, the reaction solution was added to a mixture of ice and t-butyl methyl ether, and the organic layer was separated. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was subjected to silica gel chromatography to obtain the title compound (24.7 g).

Workup

  1. customthe ice bath was removed
  2. stirringThe mixture was further stirred at room temperature
  3. stirringAfter stirring overnight
  4. additionthe reaction solution was added to a mixture of ice and t-butyl methyl ether
  5. customthe organic layer was separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe drying agent was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto obtain a residue

Sources & evidence

ORD record
ord-7d23689162d447048866ac4de0651728
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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