1-Adamantanol → 3-(1-Admantyl)-4'-iodobiphenyl-4-ol

HRID 710463노트

반응식

HRID 710463 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15]12(O)[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2>CC(O)=O.CCOC(C)=O>[C:15]12([C:10]3[CH:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=4)[CH:13]=[CH:12][C:11]=3[OH:14])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2

참가 물질

5

반응물 2

HCID 641521-AdamantanolHCID 20640304-Hydroxy-4'-iodobiphenyl

생성물 1

HCID 871266403-(1-Admantyl)-4'-iodobiphenyl-4-ol

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 4′-iodobiphenyl-4-ol (0.332 g, 2 mmol) and 1-admantanol (0.15 g, 0.51 mmol) in AcOH (2 ml) concentrated H2SO4 (0.5 ml) was added and the reaction mixture was stirred for 50 h at room temperature. This was diluted to 100 ml with EtOAc and washed with NaHCO3 solution, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was crystallized from MeOH to give the product (0.195 g; 93%), as a colourless paste. 1H NMR (CDCl3) 1.78 (m, 6H); 2.07 (s, 3H); 2.15 (s, 6H); 6.69 (d, 1H, J=8.15 Hz); 7.21-7.28 (m, 3H); 7.37 (d, 1H, J=2.28 Hz); 7.69 (d, 2H, J=8.45 Hz).

후처리

  1. additionwas added
  2. washwashed with NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was crystallized from MeOH
  7. customto give the product (0.195 g; 93%)

출처 및 근거

ORD 기록
ord-a7276908eb5d46acb1f31a4b8b789464
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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