Allyl bromide → HCID 69516190, compound

HRID 1373760Notes

Reaction equation

HRID 1373760 reaction equation
[Si:1]([O:18][C:19]1[CH:20]=[CH:21][C:22]([OH:36])=[C:23]([N:25]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])[CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37](Br)[CH:38]=[CH2:39].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:39]([O:36][C:22]1[CH:21]=[CH:20][C:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:24][C:23]=1[N:25]1[C:33](=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]1=[O:35])[CH:38]=[CH2:37]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 69516971HCID 69516971, compound

Product 1

HCID 69516190HCID 69516190, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of Example 73C (7 g, 14.2 mmol), allyl bromide (1.84 mL, 21.27 mmol) and K2CO3 (3.92 g, 28.36 mmol) in anhydrous acetone (200 mL) were stirred, and refluxed overnight. The suspension was filtered, and dried with silica gel powder (20 g). 15% ethyl acetate in hexanes (2 L) was used to run flash chromatography to give the title compound (6.74 g, 89%). MS (DCI) m/z 551.13 (M+NH4)+; 1H NMR (300 MHz, CDCl3) δ ppm 1.09 (s, 9H) 4.37–4.43 (m, 2 H) 5.02–5.22 (m, 2 H) 5.83 (m, 1 H) 6.65–6.69 (m, 2 H) 6.83 (d, J=2.37 Hz, 1 H) 7.34–7.47 (m, 6 H) 7.70–7.78 (m, 6 H) 7.89–7.94 (m, 2 H).

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe suspension was filtered
  3. customdried with silica gel powder (20 g)

Sources & evidence

ORD record
ord-4f1f30cfb308423f8364c5b1a8886590
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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