Triphenylphosphine → HCID 19603838, compound

HRID 1604691Notes

Reaction equation

HRID 1604691 reaction equation
[OH:1][CH2:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:4]=1[O:5][CH:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:19]([C:23]1[N:24]=[C:25]([C:28]2[O:29][C:30]3[CH:36]=[CH:35][C:34](O)=[CH:33][C:31]=3[CH:32]=2)[S:26][CH:27]=1)([CH3:22])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:19]([C:23]1[N:24]=[C:25]([C:28]2[O:29][C:30]3[CH:36]=[CH:35][C:34]([O:1][CH2:2][C:3]4[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[C:4]=4[O:5][CH:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:33][C:31]=3[CH:32]=2)[S:26][CH:27]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 108586652-(4-Tert-butylthiazol-2-yl)-5-hydroxybenzofuranHCID 19603829HCID 19603829, compound

Product 1

HCID 19603838HCID 19603838, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 2-(2-hydroxymethyl-6-methoxyphenoxy)propionate (1.97 g), 2-(4-tert-butylthiazol-2-yl)-5-hydroxybenzofuran (1.83 g), and triphenylphosphine (2.83 g) in tetrahydrofuran (20 ml) was added a solution of diethyl azodicarboxylate (1.67 g) in tetrahydrofuran (2 ml) under ice-cooling. The mixture was stirred at the same temperature for an hour and at room temperature for an hour. The mixture was concentrated under reduced pressure and the residue was subjected to a column of silica gel (250 ml) eluting with a mixed solvent of n-hexane and ethyl acetate (7:1) to give ethyl 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}-6-methoxyphenoxy}propionate (2.31 g).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. washeluting with a mixed solvent of n-hexane and ethyl acetate (7:1)

Sources & evidence

ORD record
ord-9573e50d341e406889621eef50cd691b
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

Loading…