Allyl bromide → HCID 18766572, compound

HRID 480701Notes

Reaction equation

HRID 480701 reaction equation
[C:1]([O:5][C:6]([C:8]([CH3:20])([O:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:21](NC(C)C)([CH3:23])[CH3:22].C(Br)C=C.C(OCC)(=O)C>C(#N)C>[CH2:23]([O:15][C:14]([C:13]1[CH:12]=[C:11]([CH:19]=[CH:18][CH:17]=1)[O:10][C:8]([CH3:20])([CH3:9])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])[CH:21]=[CH2:22]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 18766473HCID 18766473, compound

Product 1

HCID 18766572HCID 18766572, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1-tert-Butoxycarbonyl-1-methylethoxy)benzoic acid (14.92 g, 53.22 mmol) was dissolved in acetonitrile (60 mL). Subsequently, diisopropylamine (8.25 g, 63.87 mmol) was added thereto. Thereafter, allyl bromide (12.87 g, 106.45 mmol) was added dropwise, and the mixture was stirred for five hours at room temperature. Ethyl acetate was added for extraction. Washing was performed sequentially with water and saturated brine, followed by drying over magnesium sulfate. The reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby a colorless oil was obtained (11.59 g, 36.19 mmol, 67.9%).

Workup

  1. washWashing
  2. dry with materialby drying over magnesium sulfate
  3. filtrationThe reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=10/1), whereby a colorless oil
  4. customwas obtained (11.59 g, 36.19 mmol, 67.9%)

Sources & evidence

ORD record
ord-3fbd7556d6424fa391dbc0ce28cb66e0
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

Loading…