4-Methoxyphenol → HCID 178472522, compound

HRID 1490140Notes

Reaction equation

HRID 1490140 reaction equation
[OH:1][C@@H:2]1[CH2:5][C@H:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:1][C@H:2]2[CH2:5][C@H:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 90154-MethoxyphenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178472520HCID 178472520, compound

Product 1

HCID 178472522HCID 178472522, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a stirred solution of ethyl cis-3-hydroxycyclobutanecarboxylate (1.32 g, 9.20 mmol), 4-methoxyphenol (3.43 g, 27.6 mmol) and triphenylphosphine (3.12 g, 11.9 mmol) in dry THF (25 ml) was added dropwise diethyl azodicarboxylate (2.07 g, 11.9 mmol) in dry THF (5 ml) under argon atmosphere at room temperature. After completion of addition, the mixture was heated to 80° C., maintained at the same temperature for 1 h, and then volatiles removed under reduced pressure. Chromatographic purification of the residue {SiO2, 150 g; hexane/ethyl acetate (20/1)} provided 1.96 g (85%) of ethyl trans-3-(4-methoxyphenoxy)cyclobutanecarboxylate as a colorless oil. 1H NMR δ56.85-6.69 (m, 4H), 4.90-4.80 (m, 1H), 4.18 (q, J=7.0 Hz. 2H), 3.76 (s, 3H), 3.20-3.09 (m, 1H), 2.78-2.62 (m, 2H), 2.5-2.35 (m, 2H), 1.29 (t, J=7.0 Hz, 3H).

Workup

  1. additionAfter completion of addition
  2. temperaturemaintained at the same temperature for 1 h
  3. customvolatiles removed under reduced pressure
  4. customChromatographic purification of the residue {SiO2, 150 g

Sources & evidence

ORD record
ord-5e264d4c27434b2ebbaa67162a52d6b3
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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