Benzyl Bromide → Benzyl 6-heptenoate

HRID 1916083Notes

Reaction equation

HRID 1916083 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].C(N(CC)CC)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOC(C)=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[C:1]([O:9][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 707056-Heptenoic acid

Product 1

HCID 14741231Benzyl 6-heptenoate

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-heptenoic acid (4.71 g, 36.75 mmol) in AcOEt (80 mL) at 0° C. were successively added triethylamine (15.3 mL, 110.24 mmol), benzyl bromide (13.1 mL, 110.24 mmol) and Bu4NI (6.79 g, 18.37 mmol). The reaction mixture was stirred at 0° C. for 2 H and concentrated in vacuo. The residue is taken up in AcOEt, the organic phase was washed with a saturated aqueous NaHCO3 and H2O. The organic phase was dried over MgSO4 and the solvent removed in vacuo. Flash chromatography of the residue on silica gel (n-heptane/EtOAc, 9:1) provided compound C-9 (6.00 g; 75%) as a colorless oil. 13C-NMR (62.89 MHz, CDCl3): 24.42, 28.34, 33.37, 34.13, 66.08, 114.73, 128.19, 128.55, 136.16, 138.37, 173.43.

Workup

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. washthe organic phase was washed with a saturated aqueous NaHCO3 and H2O
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent removed in vacuo
  6. customFlash chromatography of the residue on silica gel (n-heptane/EtOAc, 9:1) provided compound

Sources & evidence

ORD record
ord-84603e604c7443e59e279995848e9cd4
Source dataset
uspto-grants-2013_12
Patent number
US08618080B2

Reaction notes

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