Phenol → HCID 56974686, compound

HRID 1490136Notes

Reaction equation

HRID 1490136 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1.[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:13]([C@H:10]1[CH2:11][CH2:12][C@H:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54142683HCID 54142683, compound

Product 1

HCID 56974686HCID 56974686, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of (1R,3S)-3-tetrahydropyranyloxycyclopentanol (2.00 g, 10.7 mmol), phenol (1.20 g, 12.0 mmol) and triphenylphosphine (3.20 g, 12.0 mmol) in dry THF (40 ml) cooled to 0° C. was added dropwise a solution of diethyl azodicarboxylate (2.60 g, 15.0 mmol) in dry THF (10 ml). The mixture was stirred for 1 h at room temperature and then the volatiles removed under reduced pressure. Chromatographic purification of the residue {SiO2, 150 g; hexane/ethyl acetate (20:1)} provided 2.16 g (77 %) of the title compound as a colorless oil: 1H NMR δ7.33-7.22 (m, 2H), 6.99-6.83 (m, 3H), 4.98-4.81 (m, 1H), 4.70-4.60 (m, 1H), 4.55-4.41 (m, 1H), 4.00-3.85 (m, 1H), 3.58-3.47 (m, 1H), 2.30-1.45 (m, 12H).

Workup

  1. customthe volatiles removed under reduced pressure
  2. customChromatographic purification of the residue {SiO2, 150 g

Sources & evidence

ORD record
ord-15b03486f2604da6bb19a199232d595a
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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