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

HRID 1504037노트

반응식

HRID 1504037 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 866951964-(Methoxycarbonyl)-4-methylcyclohexyl 4-nitrobenzoate수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-127f981b3e95452d842c2f4ec43dde78
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212190B2

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