4-Nitrobenzoic Acid → 4-(Methoxycarbonyl)-4-methylcyclohexyl 4-nitrobenzoate

HRID 1504037ノート

反応式

HRID 1504037 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][C:5]([CH3:12])([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:1][CH:2]2[CH2:3][CH2:4][C:5]([C:8]([O:10][CH3:11])=[O:9])([CH3:12])[CH2:6][CH2:7]2)=[O:21])=[CH:23][CH:24]=1)([O-:15])=[O:14]

参加物

6

反応物 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 13236236Methyl 4-hydroxy-1-methylcyclohexane-1-carboxylate

生成物 1

HCID 866951964-(Methoxycarbonyl)-4-methylcyclohexyl 4-nitrobenzoate収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 4-hydroxy-1-methylcyclohexane-1-carboxylate (5.8 g, 33.68 mmol, 1.00 equiv) and 4-nitrobenzoic acid (11.26 g, 67.38 mmol, 2.00 equiv) in 80 mL of anhydrous THF was added PPh3 (17.67 g, 67.37 mmol, 2.00 equiv) at room temperature. Then DIAD (13.62 g, 67.36 mmol, 2.00 equiv) was added dropwise and the resulting solution was stirred for 2 h at room temperature. The reaction was quenched water, extracted with 3×150 mL of ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/50) to give 4-(methoxycarbonyl)-4-methylcyclohexyl 4-nitrobenzoate (5.5 g, 51%) as a white solid.

後処理

  1. customThe reaction was quenched water
  2. extractionextracted with 3×150 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-127f981b3e95452d842c2f4ec43dde78
出典データセット
uspto-grants-2015_12
特許番号
US09212190B2

反応ノート

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