Allyl bromide → HCID 72270955, compound

HRID 712792Notes

Reaction equation

HRID 712792 reaction equation
[Si:1]([O:18][CH2:19][CH:20]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:21][CH:22]=[CH2:23])([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.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:41](Br)[CH:42]=[CH2:43]>CN(C=O)C.O>[CH2:43]([N:24]([CH:20]([CH2:21][CH:22]=[CH2:23])[CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26])[CH:42]=[CH2:41]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 72501553HCID 72501553, compound

Product 1

HCID 72270955HCID 72270955, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(1-((tert-butyldiphenylsilyl)oxy)pent-4-en-2-yl)-4-methylbenzenesulfonamide (D9) (13 g, 26.33 mmol) in DMF (80 ml), Cs2CO3 (12.86 g, 39.49 mmol) and allyl bromide (1.8 ml, 21.06 mmol) were added and the mixture was stirred at RT for 4 hrs. The reaction mixture was diluted with water (40 ml) and extracted with EtOAc (3×60 ml). The combined organic phases were evaporated and the resulting residue was was purified by Biotage SNAP-Si (100 g) cartridge eluting with a mixture cycloexane/EtOAc from 100/0 to 90/10. Collected fractions after solvent evaporation afforded the title compound (D10) (10.7 g).

Workup

  1. extractionextracted with EtOAc (3×60 ml)
  2. customThe combined organic phases were evaporated
  3. customthe resulting residue was was purified by Biotage SNAP-Si (100 g) cartridge
  4. washeluting with a mixture cycloexane/EtOAc from 100/0 to 90/10
  5. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-3ef8238718ce469098c02d604f4aad76
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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