Allyl bromide → tert-Butyl{2-[4-(allyloxy)phenyl]ethyl}carbamate

HRID 1433242Notes

Reaction equation

HRID 1433242 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[C:11]([O:15][C:16](=[O:27])[NH:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([CH3:14])([CH3:13])[CH3:12]>C(#N)C>[C:11]([O:15][C:16](=[O:27])[NH:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:3][CH:2]=[CH2:1])=[CH:22][CH:21]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 57933192tert-Butyl{2-[4-(allyloxy)phenyl]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Allyl bromide (2.10 ml, 24.8 mmol) was added in one portion to a suspension of potassium carbonate (4.40 g, 31.8 mmol) and tert-butyl[2-(4-hydroxyphenyl)ethyl]carbamate (Prepared according to Journal of Organic Chemistry 1999, 64, 1074, 5.00 g, 21.1 mmol) in acetonitrile (50 ml) at room temperature. The reaction was stirred for 12 hours and the solvent removed in vacuo. Diethyl ether (50 ml) and water (20 ml) were added and the organics separated, washed with water (20 ml), dried (magnesium sulphate) and the solvent removed in vacuo to yield a clear oil. The oil was purified by column chromatography on silica gel eluting with ethyl acetate:pentane (25/75 by volume) to furnish the title compound as a white solid, 3.80 g.

Workup

  1. customthe solvent removed in vacuo
  2. additionDiethyl ether (50 ml) and water (20 ml) were added
  3. washthe organics separated, washed with water (20 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customto yield a clear oil
  7. customThe oil was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-5c17df67ab7b485a8b1aadaaf63b8585
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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