Benzyl Bromide → Benzyl 6-heptenoate

HRID 605573

反応式

HRID 605573 の反応式
[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]

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 707056-Heptenoic acid

生成物 1

HCID 14741231Benzyl 6-heptenoate

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6db620ee6cfe4d1fa9f80f861b1d3444
出典データセット
uspto-grants-2011_03
特許番号
US07915240B2

関連ノート

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