Acetic Acid → (R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

HRID 1087662노트

반응식

HRID 1087662 반응식
C[Li].[CH:3]1([C@:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([OH:13])[C:10]([OH:12])=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:20](O)(=O)C.O>CCOCC.C1COCC1>[CH:3]1([C@@:9]([OH:13])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[O:12])[CH3:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 777377Cyclohexylphenylglycolic acid, (-)-HCID 178418348HCID 178418348, 화합물

생성물 1

HCID 15030055(R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 315 ml of 1.4M CH3Li (0.44 mole) in ether and 750 ml of THF at room temperature was added a solution of 26 g (0.11 mole) of (R)-cyclohexylmandelic acid, prepared by the method of R. B. Barlow, F. M. Franks, and J. D. M. Pearson, J. Med. Chem., 16, 439 (1973), in THF. Following the addition, the mixture was stirred at room temperature for 3.5 hours and then brought to reflux for 3 hours. The mixture was cooled and then added dropwise to a mixture of 300 ml of glacial acetic acid and 700 ml of water. This mixture was extracted with ether, the organic layer was separated, washed with water and saturated aqueous sodium bicarbonate, dried, and the solvent removed. The mixture was distilled to give 20 g of clear oil (bp 120° C., 0.1 mm Hg), NMR (chloroform-d) δ7.5(m, 5H), 4.5(S, 1H), 2.4(t, 1H), 2.0(s, 3H), 1.9-1.0(m, 10H).

후처리

  1. customprepared by the method of R
  2. additionthe addition
  3. temperatureto reflux for 3 hours
  4. temperatureThe mixture was cooled
  5. extractionThis mixture was extracted with ether
  6. customthe organic layer was separated
  7. washwashed with water and saturated aqueous sodium bicarbonate
  8. customdried
  9. customthe solvent removed
  10. distillationThe mixture was distilled

출처 및 근거

ORD 기록
ord-d1c5336e13e64664b508272c15d968ac
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05036107

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