Methyl bromoacetate → HCID 86623633, 화합물

HRID 1821053노트

반응식

HRID 1821053 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C1COCC1.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)/[C:8](=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])/[CH2:7][CH2:6]2

참가 물질

5

반응물 2

HCID 60984Methyl bromoacetateHCID 787875-Methoxyindan-1-one

생성물 1

HCID 86623633HCID 86623633, 화합물수율 72.9%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 5-methoxy-1-indanone (2.50 g, 15.4 mmol) and methyl bromoacetate (1.84 mL, 20.0 mmol) in THF (15 mL) was added dropwise to a mixture of activated zinc dust (1.51 g, 23.1 mmol) in THF (10 mL). During the addition the reaction mixture reached reflux temperature, which was maintained for an additional hour after the addition was completed. After cooling to ambient temperature, the reaction mixture was poured into ice-cold 2.0 N HCl and extracted into EtOAc. The organic layer was washed with H2O, brine, dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (10% EtOAc/hexanes) on SiO2 afforded 2.45 g of the title compound: 1H NMR (CDCl3) δ 3.04-3.07 (m, 2H), 3.30-3.33 (m, 2H), 3.77 (s, 3H), 3.85 (s, 3H), 6.19 (t, 1H, J=2.5 Hz), 6.83 (dd, 1H, J=2.3, 8.7 Hz), 6.85 (s, 1H), 7.52 (d 1H J=8.5 Hz).

후처리

  1. additionDuring the addition the reaction mixture
  2. temperaturereached reflux temperature, which
  3. temperaturewas maintained for an additional hour
  4. additionafter the addition
  5. extractionextracted into EtOAc
  6. washThe organic layer was washed with H2O, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by flash chromatography (10% EtOAc/hexanes) on SiO2

출처 및 근거

ORD 기록
ord-f27dbbe42c1d4f4da43803b752060909
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605171B2

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