Diethyl Ether → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenol

HRID 1074475ノート

反応式

HRID 1074475 の反応式
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CCOCC.[H-].C([Al+]CC(C)C)C(C)C>O>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][CH:18]([OH:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 127882083-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenoneHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 127882863-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenol収率 25%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-30 °C

実験手順

To a -30° C. solution of 1.00 g. (3.18 mmole) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenone in 60 ml. of ether was added dropwise 6.3 ml. of a 1 M (in toluene) diisobutylaluminum hydride solution. The reaction was stirred 30 min. longer at -30° C. and then added to 1.5 l. water. The quenched solution was extracted with three 400 ml. portions of ether and the combined extracts washed twice with 125 ml. of saturated sodium chloride and dried over magnesium sulfate. After evaporation the crude product was purified via column chromatography on 50 g. of florial eluted with ether to yield an oil. Crystallization of the oil from pentane gave 256 mg. (25%) of the title product.

後処理

  1. customTo a -30° C.
  2. additionadded to 1.5 l
  3. extractionThe quenched solution was extracted with three 400 ml
  4. washportions of ether and the combined extracts washed twice with 125 ml
  5. dry with materialof saturated sodium chloride and dried over magnesium sulfate
  6. customAfter evaporation the crude product
  7. customwas purified via column chromatography on 50 g
  8. washof florial eluted with ether
  9. customto yield an oil
  10. customCrystallization of the oil from pentane
  11. customgave 256 mg

出典と根拠

ORDレコード
ord-b82452f557b84f9d91f117af8fca164c
出典データセット
uspto-grants-1983_07
特許番号
US04391827

反応ノート

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