2-Bromopropane → 3-(1-Admantyl)-4-isopropoxybenzaldehyde

HRID 710448노트

반응식

HRID 710448 반응식
[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[OH:19])[CH:14]=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O-])([O-])=O.[K+].[K+].Br[CH:27]([CH3:29])[CH3:28]>CN(C=O)C.CCOC(C)=O>[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH:27]([CH3:29])[CH3:28])[CH:14]=[O:15])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

참가 물질

6

반응물 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 34078923-(1-Admantyl)-4-hydroxybenzaldehyde

생성물 1

HCID 871266563-(1-Admantyl)-4-isopropoxybenzaldehyde수율 86%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred suspension of 3-(1-admantyl)-4-hydroxybenzaldehyde (0.5 g, 1.95 mmol) and K2CO3 (0.276 g, 2 mmol) in anhydrous DMF (5 ml) was added 2-bromopropane (1 ml) and the mixture was reflux for 2 h. The reaction mixture was brought to room temperature and diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was crystallized from MeOH to give the title compound (0.25 g, 86%), as a colourless solid. 1H-NMR (CDCl3) 1.42 (d, 6H, J=6 Hz); 1.76 (broad s, 6H); 2.07 (broad s, 3H); 2.12 (s, 6H); 4.69-4.78 (m, 1H); 6.91 (d, 1H, J=8.44 Hz); 7.66 (dd, 1H, J=2.13, 8.45 Hz); 7.76 (d, 1H, J=2.11 Hz); 9.84 (s, 1H).

후처리

  1. temperaturethe mixture was reflux for 2 h
  2. customwas brought to room temperature
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was crystallized from MeOH

출처 및 근거

ORD 기록
ord-6ee090b971774480b882f9a9aa67a059
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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