Toluene → Methyl 6-(spiro[5.5]undecan-3-yloxy)-2-naphthoate

HRID 2404096노트

반응식

HRID 2404096 반응식
[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH:3]([OH:12])[CH2:2]1.[CH3:13][O:14][C:15]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22](O)[CH:23]=2)[CH:18]=1)=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[CH2:5]1[C:6]2([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:1][CH2:2][CH:3]([O:12][C:22]2[CH:23]=[C:24]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:15]([O:14][CH3:13])=[O:16])[CH:26]=[CH:25]3)[CH2:4]1

참가 물질

7

반응물 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 390995Methyl 6-hydroxy-2-naphthoateHCID 66926515Spiro[5.5]undecan-3-ol

생성물 1

HCID 66926514Methyl 6-(spiro[5.5]undecan-3-yloxy)-2-naphthoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of spiro[5.5]undecan-3-ol (0.999 g, 0.00593 mol), 6-hydroxy-naphthalene-2-carboxylic acid methyl ester (1.00 g, 0.00494 mol) and triphenylphosphine (1.56 g, 0.00593 mol) in toluene (10 mL, 0.1 mol) was heated to reflux. Diisopropyl azodicarboxylate (1.17 mL, 0.00593 mol) was then added dropwise and the resulting mixture was refluxed for 6 hours. The mixture was then diluted with dichloromethane and subjected to chromatographic purification with ethyl acetate:hexane (0:100 to 40:60) to give methyl 6-(spiro[5.5]undecan-3-yloxy)-2-naphthoate as a white solid. (1.09 g, 62%). 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 8.01 (dd, J=8.7, 1.7 Hz, 1H), 7.84 (d, J=9.6 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.17 (m, 2H), 4.45 (m, 1H), 3.97 (s, 3H), 1.93-1.28 (m, 18H).

후처리

  1. temperaturewas heated to reflux
  2. temperaturethe resulting mixture was refluxed for 6 hours
  3. customsubjected to chromatographic purification with ethyl acetate:hexane (0:100 to 40:60)

출처 및 근거

ORD 기록
ord-937ea7c93b8e4d7c98344f9c5fbec190
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802659B2

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