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

HRID 2356125ノート

反応式

HRID 2356125 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dab765b87b664b5d826a57568fdc2afc
出典データセット
uspto-grants-2010_07
特許番号
US07754886B2

反応ノート

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