Benzyl Bromide → Benzyl 6-heptenoate

HRID 605573

Reaction equation

HRID 605573 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 2H 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 C-9 (6.00 g 75%) as a colorless oil

Sources & evidence

ORD record
ord-6db620ee6cfe4d1fa9f80f861b1d3444
Source dataset
uspto-grants-2011_03
Patent number
US07915240B2

Linked notes

Loading…