Allyl bromide → HCID 58864607, compound

HRID 1353165Notes

Reaction equation

HRID 1353165 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH2:3]1.[H-].[Na+].[CH2:23](Br)[CH:24]=[CH2:25].C(OCC)(=O)C>CN(C)C=O.O1CCCC1>[CH2:25]([O:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH2:3]1)[CH:24]=[CH2:23]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11492838methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate

Product 1

HCID 58864607HCID 58864607, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.3 g of methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate are dissolved in 40 ml of dimethylformamide and 1.3 g of sodium hydride (60% strength suspension in paraffin oil) are added. After 40 minutes of stirring, 4 ml of allyl bromide, dissolved in 20 ml of tetrahydrofuran, are added. After 3 hours, 300 ml of ethyl acetate are added and the mixture is washed three times with saturated sodium chloride solution. The combined organic phases are dried over sodium sulfate and the solvents are then removed under reduced pressure. The resulting residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=50:1→5:1. This gives 2.1 g of methyl 2-((1R,3S)-3-allyloxycyclohexyloxymethyl)-6-methylbenzoate as a yellow oil. C19H26O4 (318.42), MS(ESI): 319 (M+H+).

Workup

  1. additionare added
  2. waitAfter 3 hours
  3. washthe mixture is washed three times with saturated sodium chloride solution
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvents are then removed under reduced pressure
  6. customThe resulting residue is purified on silica gel using the mobile phase n-heptane

Sources & evidence

ORD record
ord-8d4a4262ffb54c49b1adf7b2af30c4d4
Source dataset
uspto-grants-2007_05
Patent number
US07220876B2

Reaction notes

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