Phenol → HCID 53977418, compound

HRID 2226585Notes

Reaction equation

HRID 2226585 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:15][C:16](=[O:25])[C@@H:17]([O:21][C:22](=[O:24])[CH3:23])[CH2:18][CH2:19][OH:20])[CH3:14].[C:26]1(O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:13]([O:15][C:16](=[O:25])[C@@H:17]([O:21][C:22](=[O:24])[CH3:23])[CH2:18][CH2:19][O:20][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:14]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11171486ethyl (2S)-2-acetyloxy-4-hydroxybutanoate

Product 1

HCID 53977418HCID 53977418, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (1.37 g, 7.9 mmol) in tetrahydrofuran (3 ml) was added to a stirred mixture of (S)-2-acetoxy-4-hydroxybutanoic acid ethyl ester (1.0 g, 5.3 mmol), phenol (0.74 g, 7.9 mmol) and triphenylphosphine (2.07 g, 7.9 mmol) in tetrahydrofuran (16 ml). After 4 days the solvent was evaporated and the residue purified by chromatography on silica with ethyl acetate/petroleum ether (60°-80°) mixtures as eluant, to give the sub-title compound (1.4 g).

Workup

  1. customAfter 4 days the solvent was evaporated
  2. customthe residue purified by chromatography on silica with ethyl acetate/petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-c1e87ff6f99243ae8eb41503172c9164
Source dataset
uspto-grants-1994_09
Patent number
US05348978

Reaction notes

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