N-Butyldiethanolamine → 2-(2'-Methoxycarbonylphenyl)-6-butyl[1,3,6,2]dioxazaborocan

HRID 60566

반응식

HRID 60566 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[B:11]([OH:13])[OH:12])=[O:4].[CH2:14]([N:18]([CH2:22][CH2:23]O)[CH2:19][CH2:20]O)[CH2:15][CH2:16][CH3:17]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[B:11]1[O:13][CH2:23][CH2:22][N:18]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:19][CH2:20][O:12]1)=[O:4]

참가 물질

4

반응물 2

HCID 7620N-ButyldiethanolamineHCID 27734962-(Methoxycarbonyl)benzeneboronic acid

생성물 1

HCID 669276852-(2'-Methoxycarbonylphenyl)-6-butyl[1,3,6,2]dioxazaborocan수율 98.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
50 °C

실험 절차

To a suspension of (2-methoxycarbonylphenyl)boronic acid (5.0 g, 27.8 mmol) in toluene (40 mL) was added N-butyldiethanolamine (4.8 mL, 29.2 mmol, 1.05 equiv.) via a syringe. The mixture was heated at 50° C. for two hours. After cooling to room temperature, the toluene was evaporated under reduced pressure and the remaining clear colorless crude oil was treated with heptanes (˜500 mL). The heptanes mixture was then sonicated ˜5 min and the resulting suspension was allowed to stand at room temperature overnight. The solid that precipitated was collected by filtration, washed with heptanes, and dried in a vacuum oven overnight to yield a white solid as the 2-(2′-methoxycarbonylphenyl)-6-butyl[1,3,6,2]dioxazaborocan. 1H NMR (DMSO-d6) δ: 7.55-7.59 (m, 1H), 7.17-7.29 (m, 2H), 7.12-7.14 (m, 1H), 3.85-3.92 (m, 2H), 3.78-3.82 (m, 1H), 3.78 (br. s., 1H), 3.67 (s, 3H), 3.26-3.30 (m, 1H), 3.12 (dt, J=5.2, 2.6 Hz, 2H), 3.03-3.11 (m, 2H), 2.41-2.49 (m, 4H), 1.45-1.55 (m, 2H), 0.98-1.05 (m, 2H), 0.83 (s, 1H), 0.71-0.77 (m, 3H). Amount obtained, 8.3 g, (98.1% yield).

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe toluene was evaporated under reduced pressure
  3. additionthe remaining clear colorless crude oil was treated with heptanes (˜500 mL)
  4. customThe heptanes mixture was then sonicated ˜5 min
  5. customThe solid that precipitated
  6. filtrationwas collected by filtration
  7. washwashed with heptanes
  8. customdried in a vacuum oven overnight

출처 및 근거

ORD 기록
ord-5fdf928c61e64d9dbd030645267cf83e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440994B2

연결된 노트

불러오는 중…