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

HRID 713877Notes

Reaction equation

HRID 713877 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-e859c160542a498cadd9dcfd47a85132
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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