Cerium(III) chloride → Methyl 4-(4-hydroxy-4-methylcyclohex-1-en-1-yl)benzoate

HRID 2356125노트

반응식

HRID 2356125 반응식
[Cl-].[Ce+3].[Cl-].[Cl-].[CH3:5][Li].[Cl-].[Li+].[O:9]=[C:10]1[CH2:15][CH2:14][C:13]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[CH:12][CH2:11]1>C1COCC1.C(OCC)C.C(OCC)(=O)C>[OH:9][C:10]1([CH3:5])[CH2:15][CH2:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=2)=[CH:12][CH2:11]1

참가 물질

8

반응물 4

HCID 24636Cerium(III) chlorideHCID 433294Lithium ChlorideHCID 22730167Methyl 4-(4-oxocyclohex-1-en-1-yl)benzoateHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 22730725Methyl 4-(4-hydroxy-4-methylcyclohex-1-en-1-yl)benzoate

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

A suspension of anhydrous cerium(III) chloride (2.71 g, 11 mmol) in THF (10 mL) at −78° C. was slowly treated with 1.5M methyllithium complexed with lithium chloride in diethyl ether (6.7 mL), warmed to room temperature over 2 hours, and added to a solution of Example 420C (1.15 g, 5.0 mmol) in THF (10 mL) at −78° C. The reaction was gradually warmed to room temperature over 4 hours, diluted with ethyl acetate (100 mL), washed with water (45 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10-30% ethyl acetate/hexanes to provide the desired product.

후처리

  1. temperatureThe reaction was gradually warmed to room temperature over 4 hours
  2. washwashed with water (45 mL) and brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 10-30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-dab765b87b664b5d826a57568fdc2afc
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754886B2

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