3-Bromophenol → Pentyl ether

HRID 439762

반응식

HRID 439762 반응식
C([Li])(C)(C)C.BrC1C=C(O)C=CC=1.[CH2:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:15][CH2:16][CH2:17][CH3:18].BrCCCCCOCC1C=CC=CC=1.C([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]1[CH:53]=[C:54]([OH:58])[CH:55]=[CH:56][CH:57]=1)C1C=CC=CC=1>O1CCCC1.C(O)C.[Pd]>[OH:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]1[CH:53]=[C:54]([OH:58])[CH:55]=[CH:56][CH:57]=1.[CH2:20]([O:19][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:21][CH2:22][CH2:23][CH3:24]

참가 물질

10

반응물 5

HCID 115633-BromophenolHCID 12743Pentyl ether2회HCID 14221121Benzyl 5-Bromoamyl EtherHCID 539069383-(Benzyloxypentyl)-phenolHCID 178418306HCID 178418306, 화합물

생성물 2

HCID 12743Pentyl etherHCID 224079723-(5-Hydroxypentyl)-phenol

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

At a temperature of -78° C., 19.4 ml of t-butyl lithium (1.7M) is added to 4.0 gm of the above 3-bromo-phenol, n-pentyl ether in 50 mls tetrahydrofuran; and to this is added 3.3 ml of a freshly prepared solution of Li2CuCl3 (0.10M/THF). The mixture is stirred for 10 minutes, and then 4.35 grams of the 1-bromo-5-benzyloxy pentane are added. The reaction is allowed to warm slowly to ambient temperature over 12 hours and is then stirred an additional 24 hours before being quenched with silica gel. After removing the solvent, the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture containing 3-(benzyloxypentyl)-phenol, n-pentyl ether. A solution of 6.0 gm of this crude mixture in ethanol is hydrogenated over 5% Pd on carbon for 5 hours. After filtering through celite and concentrating, pure 3-(5-hydroxypentyl)-phenol, n-pentyl ether is obtained as a clear oil by HPLC chromatography.

후처리

  1. stirringis then stirred an additional 24 hours
  2. custombefore being quenched with silica gel
  3. customAfter removing the solvent
  4. customthe mixture is chromatographed over silica gel (1:1 hexane:ether)
  5. customto yield a crude mixture
  6. filtrationAfter filtering through celite
  7. concentrationconcentrating

출처 및 근거

ORD 기록
ord-89310f4a37c245118727c13c1cf2e375
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516767

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