3,4-dihydro-2H-pyran → 2-(5-Bromo-2-methyl-2-phenylpentyloxy)-tetrahydropyran

HRID 47992

반응식

HRID 47992 반응식
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Br:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:12][OH:13]>>[Br:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:12][O:13][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

참가 물질

3

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 113458925-Bromo-2-methyl-2-phenylpentan-1-ol

생성물 1

HCID 114846082-(5-Bromo-2-methyl-2-phenylpentyloxy)-tetrahydropyran수율 96.2%

실험 절차

Under N2 atmosphere, 3,4-dihydro-2H-pyran (8.19 g, 98 mmol) was added drop-wise to a stirred solution of 5-bromo-2-methyl-2-phenyl-pentan-1-ol (20 g, 78 mmol) at −5° C. The reaction mixture was allowed to warm to rt and stirred for 5 h. The solution was filtered through aluminum oxide (100 g), which was washed with CH2Cl2 (500 mL). The filtrate was concentrated in vacuo to furnish 2-(5-bromo-2-methyl-2-phenyl-pentyloxy)-tetrahydropyran (25.23 g, 96.2%) as an oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 7.26-7.08 (m, 5H), 4.45 (m, 1H), 3.72 (m, 1H), 3.58 (m, 1H), 3.35-3.05 (m, 2H), 3.28 (t, J=6.6, 2H), 1.95-1.39 (m, 10H), 1.25 (s, 3H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm) 145.37, 128.14, 126.51, 126.03, 99.06, 98.92, 61.91, 61.80, 41.82, 41.74, 37.58, 37.43, 34.65, 30.61, 27.88, 25.58, 23.03, 22.89, 19.39, 19.32. HRMS (HR, LSIMS, nba): Calcd. for C17H26O2Br (MH+): 341.1116, found: 341.1127.

후처리

  1. filtrationThe solution was filtered through aluminum oxide (100 g), which
  2. washwas washed with CH2Cl2 (500 mL)
  3. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-233a2f7c11684291ad93f3fbfa876a1f
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699910B2

연결된 노트

불러오는 중…