Isopropanol → 2-(2-Chloro-4-isopropoxyphenoxy)-1,3-thiazole

HRID 404894Notes

Reaction equation

HRID 404894 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1.[CH:15](O)([CH3:17])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH:15]([CH3:17])[CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 691693943-Chloro-4-(1,3-thiazol-2-yloxy)phenol

Product 1

HCID 694369042-(2-Chloro-4-isopropoxyphenoxy)-1,3-thiazoleYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of Example 9B (2.3 g, 0.01 mol), isopropanol (1.2 mL, 0.015 mol) and triphenylphosphine (3.93 g, 0.015 mol) in dry tetrahydrofuran was added diethyl azodicarboxylate (2.61 g, 0.015 mol) drop wise and the reaction was stirred at room temperature overnight. The solvent was removed and the residue was purified on silica gel (ethyl acetate/hexane, 5˜35%) to give 2.4 g of product as a light yellow oil (89% yield), 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=5.88 Hz, 6H) 4.42-4.57 (m, 1H) 6.76-6.86 (m, 2H) 6.99 (d, J=2.94 Hz, 1H) 7.19 (d, J=3.68 Hz, 1H) 7.23 (s, 1H), MS (ESI) m/z 269.9 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on silica gel (ethyl acetate/hexane, 5˜35%)

Sources & evidence

ORD record
ord-97f736f9d04f494ca8469431e78d3212
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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