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

HRID 1660055노트

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HRID 1660055 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
-30 °C

실험 절차

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 1. 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.

후처리

  1. customTo a -30° C.
  2. additionadded to 1.5 1
  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

출처 및 근거

ORD 기록
ord-6543b6a5604e45eb9c06b8c3c18f8043
출처 데이터셋
uspto-grants-1981_12
특허 번호
US04306097

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