Benzyl Bromide → Benzyl 6-heptenoate

HRID 605573

반응식

HRID 605573 반응식
[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]

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 707056-Heptenoic acid

생성물 1

HCID 14741231Benzyl 6-heptenoate

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6db620ee6cfe4d1fa9f80f861b1d3444
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915240B2

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