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

HRID 2404096Notes

Reaction equation

HRID 2404096 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-937ea7c93b8e4d7c98344f9c5fbec190
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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