Water → 1-(2',4'-Dichloro-biphenyl-4-yl)-6-hydroxy-hexan-1-one

HRID 227892

반응식

HRID 227892 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])=[CH:11][CH:10]=1.B(O[O-])=[O:23].[Na+].O>B1C2CCCC1CCC2>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:23])=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 517072Sodium PerborateHCID 577572631-(2',4'-Dichloro-biphenyl-4-yl)-hex-5-en-1-one

생성물 1

HCID 248965951-(2',4'-Dichloro-biphenyl-4-yl)-6-hydroxy-hexan-1-one

시약·촉매·용매 1

HCID 789669-Borabicyclo(3.3.1)nonane용매

실험 절차

1-(2′,4′-Dichloro-biphenyl-4-yl)-hex-5-en-1-one (1.1 g) was dissolved in 0.5 M 9-BBN (6.9 mL) and stirred at room temperature for 4 hours. Sodium perborate (1 g) was added and the mixture stirred at room temperature for 1 hour. Water (3 mL) was added and the mixture stirred at 50° C. for 2 hours, then overnight at room temperature. The mixture was extracted with ether, dried, and evaporated to give an oil. The oil was purified by column chromatography to give an oil which solidified to a white amorphous solid on standing, and which was recrystallised from ether/petrol to give the title compound as a white powder. 13C NMR (CDCl3): δ23.9, 25.5, 32.5, 38.6, 62.7, 127.4, 128.0, 129.7, 129.9, 131.9, 133.1, 134.5, 136.3, 138.0, 142.8 and 199.9. 1H NMR (CDCl3): δ 1.45 (2H, m), 1.60 (2H, m), 1.80 (2H, m), 3.01 (2H, t, J=6.5 Hz), 3.68 (2H, t, J=6.5 Hz), 7.28 (2H, d, J=8.2 Hz), 7.30 (1H, s), 7.50 (2H, m) and 8.01 (2H, d, J=8.2 Hz).

후처리

  1. stirringthe mixture stirred at room temperature for 1 hour
  2. stirringthe mixture stirred at 50° C. for 2 hours
  3. customovernight
  4. customat room temperature
  5. extractionThe mixture was extracted with ether
  6. customdried
  7. customevaporated
  8. customto give an oil
  9. customThe oil was purified by column chromatography
  10. customto give an oil which
  11. customwhich was recrystallised from ether/petrol

출처 및 근거

ORD 기록
ord-d12c44ba7bec4468944f2414095dda3a
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560597B2

연결된 노트

불러오는 중…