3,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether → 2,6-Diphenyl-4-decyloxy-phenol

HRID 1281437

반응식

HRID 1281437 반응식
[CH2:1]([O:11][C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([O:24]COCCOC)=[C:14]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>C(Cl)Cl.[Zn+2].[Br-].[Br-]>[C:31]1([C:14]2[CH:13]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:17]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:15]=2[OH:24])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

참가 물질

4

반응물 1

HCID 222374833,5-Diphenyl4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether

생성물 1

HCID 222375862,6-Diphenyl-4-decyloxy-phenol수율 79.1%

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 3,5-diphenyl-4-[(2-methoxyethoxy)methoxy]-phenyl decyl ether (0.880 g, 1.793 mmol) and ZnBr2 (2.019 g, 8.967 mmol) in methylene chloride (10 ml) under nitrogen was stirred at room temperature. After ˜48 h, the reaction mixture was concentrated in vac and the residue was taken up in EtOAc (60 ml) and saturated NaHCO3 solution (20 ml). The layers were shaken and separated and the organic layer was washed with saturated NaHCO3 solution (2×10 ml), water (3×10 ml), brine (1×10 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane and 1% EtOAc/Hex) to give the product as a light brown oil (0.571 g, 79%); 1H NMR (400 MHz, DMSO-d6) δ 0.83-0.88 (m, 3H), 1.20-1.36 (m, 12H), 1.36-1.45 (m, 2H), 1.65-1.73 (m, 2H), 3.96 (t, J=6.6 Hz, 2H), 6.77 (s, 2H), 7.31-7.36 (m, 2H), 7.40-7.45 (m, 4H), 7.54-7.58 (m, 4H), 7.80 (s, 1H); IR (film) 3550, 2940, 1600, 1460, 1180 cm−1; mass spectrum [EI], m/z 402 M+.

후처리

  1. concentrationthe reaction mixture was concentrated in vac
  2. stirringThe layers were shaken
  3. customseparated
  4. washthe organic layer was washed with saturated NaHCO3 solution (2×10 ml), water (3×10 ml), brine (1×10 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vac
  8. customdried
  9. customThe residue was purified by flash chromatography (hexane and 1% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-e106c9297f93465b87eb7a8d856771e7
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451827B2

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