Potassium Carbonate → 3,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether

HRID 1281436

반응식

HRID 1281436 반응식
[C:1]1([C:7]2[CH:8]=[C:9]([OH:26])[CH:10]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]=2[O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>CN(C=O)C>[CH2:34]([O:26][C:9]1[CH:10]=[C:11]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:12]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 163141-Iododecane2회HCID 222375693,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-phenol

생성물 1

HCID 222374833,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
63 °C

실험 절차

To a stirred solution of 3,5-diphenyl-4-[(2-methoxyethoxy)methoxy]-phenol (0.946 g, 2.7 mmol) in DMF (15ml) was added K2CO3 (0.746 g, 5.4 mmol) and iododecane (1.632 g, 5.4 mmol). The reaction mixture was warmed to ˜63° C. After ˜20 h, additional K2CO3 (0.373 g, 2.7 mmol) and iododecane (0.816 g, 2.7 mmol) were added. Heating was continued for an additional 20 h followed by stirring at room temperature for 20 h. The reaction mixture was concentrated in vac and the residue taken up in EtOAc (50 ml) and water (20 ml). The layers were shaken and separated and the organic layer was washed with water (3×10 ml), brine (2×10 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane and 5% EtOAc/Hex) to give the product as a brown oil (0.897 g, 68%); 1H NMR (400 MHz, DMSO-d6) δ 0.83-0.88 (m, 3H), 1.20-1.37 (m, 12H), 1.37-1.46 (m, 2H), 1.68-1.76 (m, 2H), 2.71-2.75 (m, 2H), 2.86-2.88 (m, 2H), 3.01 (s, 3H), 4.03 (t, J=6.4 Hz, 2H), 4.22 (s, 2H), 6.87 (s, 2H), 7.34-7.39 (m, 2H), 7.42-7.48 (m, 4H), 7.56-7.60 (m, 4H); IR (film) 2940, 1590, 1460, 1190 cm−1; mass spectrum [(+)ESI], m/z 508 (M+NH4)+.

후처리

  1. temperatureHeating
  2. waitwas continued for an additional 20 h
  3. concentrationThe reaction mixture was concentrated in vac
  4. stirringThe layers were shaken
  5. customseparated
  6. washthe organic layer was washed with water (3×10 ml), brine (2×10 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vac
  10. customdried
  11. customThe residue was purified by flash chromatography (hexane and 5% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-f2b8359d64564c94b8d7eb6b6bc0ad0b
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451827B2

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