3-Bromophenol → Pentyl ether

HRID 36149

反応式

HRID 36149 の反応式
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]

参加物

10

反応物 5

HCID 115633-BromophenolHCID 12743Pentyl ether2 回HCID 14221121Benzyl 5-Bromoamyl EtherHCID 539069383-(Benzyloxypentyl)-phenolHCID 178418306HCID 178418306、化合物

生成物 2

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a33eb14b5e2546bc96b1dbc59ac08fd1
出典データセット
uspto-grants-1995_05
特許番号
US05412137

関連ノート

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